4,022 Works

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-XKOXVLDNAL-UHFFFADPSC-NUHFF-NMBEL-NUHFF-ZZZ

Claudine Herlan
The precursor used for this conversion was obtained from the reaction: https://www.chemotion-repository.net/pid/13201The crude macrocycle tert-butyl 3-((3S,6S,9S,14aR)-6-(4-(tert-butoxy)benzyl)-9-(sec-butyl)-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)propanoate (33.0 mg, 53.7 μmol, 1.00 equiv) was dissolved in 4.50 mL 95% trifluoroacetic acid in 0.5 mL of dichloromethane and stirred for at least 1 h. The solvent was removed under air stream and the residue was dissolved in a mixture of acetonitrile and water.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-TZKVYDXSGF-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Helena Šimek
To a stirred solution of 2-iodoaniline (250.0 mg, 1.14 mmol, 1.0 equiv.) and pyridine (186.2 mg, 0.19 mL, 2.35 mmol, 2.1 equiv.) in CH2Cl2 (2.5 mL) was added p-toluenesulfonyl chloride (261.7 mg, 1.37 mmol, 1.2 equiv.) at 0 °C. The reaction was stirred at 0 °C for 1 h, and then allowed to warm to 21 °C and stir until the complete consumption of starting material (monitored by TLC, 4 h). The reaction mixture was...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-FEDJQHYSUP-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Daniel Knoll
A 500 mL Schlenk flask was charged with 4,16-dibromo­[2.2.]­para­cyclo­phane (1.50 g, 4.10 mmol, 1.00 equiv.) and dry THF (100 mL). The reaction mixture was cooled to –78 °C and n-BuLi (2.00 mL, 4.92 mmol, 1.20 equiv.) was added dropwise via syringe. The solution became pink in color and faded to a pale yellow. This step was allowed to proceed for 30 min. Then chlorodiphenylphosphine (1.51 mL, 1.81 g, 8.20 mmol, 2.00 equiv.) was added. The...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ROUMDNPPUP-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Daniel Knoll
In a vial fitted with a magnetic stirring bar, potassium 4-trifluoroborate[2.2]paracyclophane (261.6 mg, 0.83 mmol, 1.50 equiv.), potassium phosphate (471.2 mg, 2.20 mmol, 4.00 equiv.), palladium acetate (6.2 mg, 0.03 mmol, 0.05 equiv.) and RuPhos (38.9 mg, 0.08 mmol, 0.15 equiv.) were placed. The vial was evacuated and backfilled with argon three times. After addition of the solvent (toluene/water 10:1, 0.1 M), the respective bromide (129 µL, 0.56 mmol, 1.00 equiv., if liquid) was added...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-HOTMMJRJOH-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
The starting material (148 mg, 430 μmol, 1.00 equiv) was dissolved in THF (6.00 mL) and water (0.6 mL). 4-Toluenesulfonic acid monohydrate (163 mg, 163 μL, 859 μmol, 2.00 equiv) and formaldehyde (339 mg, 311 μL, 4.3 mmol, 10.0 equiv) were added. The reaction was stirred in the microwave for 4 hours at 120°C, 10 bar and 30 Watt.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-SPHVUXIZEZ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Isabelle Wessely
1-[4-(1-Hydroxyethyl)phenyl]ethanol (3.58 g, 21.5 mmol, 1.00 equiv) was dissolved in 150 mL of dichloromethane at 0 °C, before hydron bromide (14.2 g, 10.0 mL, 57.9 mmol, 2.69 equiv) was added. After the reaction was stirred for 3.5 h at this temperature, 70 mL water were added. The phases were separated and the organic phase was washed with a saturated NaHCO3-solution, water and brine before being dried over sodium sulfate. The solvent was removed under reduced...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-BHYVHYPBRY-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Christoph Schissler
4-Formylbenzoic acid (7.93 g, 52.8 mmol, 1.00 equiv.) was dissolved in DMF (197 mL) and K2CO3 (14.1 g, 102 mmol, 1.94 equiv.) and iodethane (10.8 mL, 20.9 g, 134 mmol, 2.54 equiv.) were added. The reaction mixture was stirred for 3 h at room temperature and quenched with water (250 mL). The aqueous phase was extracted with Et2O (2 × 200 mL ), the combined organic phases were washed with brine (2 × 200 mL),...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ABTZHDQWMU-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Jérôme Klein
To a solution of 4-phenyltetrazolo[1,5-a]quinoxaline (60.0 mg, 243 μmol, 1.00 equiv), copper sulfate (69.7 mg, 437 μmol, 1.80 equiv), sodium ascorbate (86.5 mg, 437 μmol, 1.80 equiv) and N-Ethyldiisopropylamine (56.5 mg, 76.1 μL, 437 μmol, 1.80 equiv) in N,N-dimethylformamide (2.00 mL) was added ethynylbenzene (44.6 mg, 48.0 μL, 437 μmol, 1.80 equiv) at 21 °C. The solution was then stirred for 24h at 120 oC. The residue was diluted with distilled water, and extracted with...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-YEYQPMMYRP-UHFFFADPSC-NUHFF-MZOEC-NUHFF-ZZZ

Alex Braun
In a vial, (E)-2,3,3-trimethyl-5-(3,3,4,4,5,5,6,6,6-nonafluorohex-1-en-1-yl)-3H-indole (110 mg, 272 µmol, 1.00 equiv.) and 77.43 mg methyl iodide (545 µmol, 2.0 equiv.) were dissolved in 0.85 mL acetonitrile and stirred for 20 h at 80 °C.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-PNJCQSRZVF-UHFFFADPSC-NUHFF-MVQBS-NUHFF-ZZZ

Christoph Schissler
5-2-Formylphenyl,10,15,20-triphenylporphyrin (40.0 mg, 62.2 µmol, 1.00 equiv.) and Ni(acac)2 (56.9 mg, 310 µmol, 5.00 equiv.) were dissolved in DMF (15 mL). The reaction mixture was stirred for 4 h at 150 °C and the solvent evaporated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-LZVFZGBIIF-UHFFFADPSC-NUHFF-NZMGP-NUHFF-ZZZ

Alex Braun
In a vial, 5-iodo-2,2,3-trimethyl-3H-indole (0.325 g, 1.14 mmol, 1.00 equiv.), palladium(II) acetate (25.6 mg, 114.0 μmol, 0.10 equiv.), tetra-n-butylammonium bromide (73.5 mg, 0.228 mmol, 0.20 equiv.) and sodium acetate (0.234 g, 2.85 mmol, 2.50 equiv.) were evacuated and flushed with argon. Then, 1H,1H,2H-perfluoro-1-octene (0.649 mg, 2.85 mmol, 2.50 equiv.) und 7.50 mL dry DMF were added and the reaction mixture was stirred for 20 h at 110 °C. After cooling down, 50 mL ethyl acetate...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-RWOLZECCEA-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Jérôme Klein
A solution of lithium diisopropylamide (97.9 mg, 914 μL, 914 μmol, 1.00M, 2.20 equiv) and THF (5.00 mL) was put under an atmosphere of dry nitrogen. Then tributylstannane (266 mg, 246 μL, 914 μmol, 2.20 equiv) was added, the yellow pale solution was stirred at 0 °C for 15 min and the temperature was decreased to -78 °C. Then a solution of 2-chloranyl-3-phenyl-quinoxaline (100 mg, 415 μmol, 1.00 equiv) in THF (2.00 mL) at -78...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-GMLILFMFND-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
In a vial, 4-(methylamino)benzaldehyde (100 mg, 740 μmol, 1.20 equiv) was dissolved in toluene (5.00 mL) and 2-amino-4-(trifluoromethyl)benzenethiol (119 mg, 617 μmol, 1.00 equiv) and p-toluenesulfonic acid monohydrate (11.7 mg, 61.7 μmol, 0.100 equiv) were added. The reaction was stirred for 18 h at 70 °C. The reaction mixture was poured into a flask and the reaction vessel was flushed with toluene to collect the material that remained in the reaction vessel.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MVJGJYRFWK-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
1H-Indole (250 mg, 2.1 mmol, 1.00 equiv) was dissolved in 10 mL of abs. methylene chloride (N2 atmosphere) and dimethylalumanylium;chloride in hexane (1 M, 2.56 mL, 2.6 mmol, 1.20 equiv) was added at 0 °C. The reaction was stirred for 15 min at 0 °C and 2-phenylacetyl chloride (330 mg, 282 μL, 2.13 mmol, 1.00 equiv) was added. The reaction was allowed to come to room temperature and was stirred at 21 °C for 14...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-VOWUHKQBOI-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
1-H Indole (1.00 g, 8.54 mmol, 1.00 equiv) was dissolved under inert atmosphere in 50 mL of dry DMF. Sodium hydride (512 mg, 12.80 mmol, 1.50 equiv) and 1-bromooctane (1.98 g, 1.77 mL, 10.2 mmol, 1.20 equiv) were added at 0 °C and the reaction was stirred over night at 21 °C.The workup of the reaction was done by pouring the reaction on ice and extraction of the organic phases with ethyl acetate. The combined...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-CCIAYANZDW-UHFFFADPSC-NUHFF-NOTDD-NUHFF-ZZZ

Christoph Schissler
1,2-Phenyl-(2-(5,10,15,20-tetraphenylporphyrin-10,15,20-triphenylporphyrin)-5-(10,15,20-triphenyporphyrin)) (2.0 mg, 1.6 µmol, 1.00 equiv.) and Zn(OAc)2 (1.2 mg, 6.5 µmol, 4.06 equiv.) were dissolved in a mixture of CHCl3 and MeOH (10:1, 2.1 mL). The reaction mixture was stirred for 30 min at 60 °C and the solvent evaporated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AMOBBDHYJV-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Steven Susanto
Methyl 2-(bromomethyl)prop-2-enoate (16.0 g, 89 mmol, 1.00 equiv) was dissolved in 200 mL of THF and 200 mL of dest. water. Ethanethioic S-acid (10.2 g, 9.54 mL, 134 mmol, 1.50 equiv) was added and the mixture was cooled to 0 °C. Disodium carbonate (14.2 g, 134 mmol, 1.50 equiv) was added and the resulting mixture was stirred at 21 °C for 2 h. After disappearance of the starting material (TLC control) the reaction was diluted...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-WVKIULBYJF-UHFFFADPSC-NUHFF-LREIQ-NUHFF-ZZZ

Christoph Schissler
1,2-Phenyl-5-(10,20-para-diethoxycarbonylphenylporphyrin-10,15,20-triphenylporphyrin) (2.2 mg, 1.8 µmol, 1.00 equiv.) and Zn(OAc)2 (3.6 mg, 19.6 µmol, 10.9 equiv.) were dissolved in a mixture of CHCl3 and MeOH (10:1, 2.1 mL). The reaction mixture was stirred for 1 h at 80 °C and the solvent evaporated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-VSSZQPPDIO-UHFFFADPSC-NUHFF-LREIQ-NUHFF-ZZZ

Christoph Schissler
1,2-Phenyl-5-(10,20-para-diethoxycarbonylphenylporphyrin-10,15,20-triphenylporphyrin) (2.0 mg, 1.6 µmol, 1.00 equiv.) and Ni(acac)2 (1.8 mg, 8.4 µmol, 5.25 equiv.) were dissolved in DMF (2 mL). The reaction mixture was stirred for 2 h at 100 °C and the solvent evaporated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-QZRDVUOPVS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle & Jérôme Klein
2-Azido-3-phenylquinoxaline, Potassium iodine and Sodium azide were dissolved in DMF and heated to reflux until TLC shows the end of reaction (3h). Ethyl acetate and dist water were then added. The organic layer was then washed with brine (3x). The organic layer was then dried over Na2SO4 and the solvent was then removed. The product was purified with chromatography column chromatography (1:10 EtOAc/Cyclohexane) to afford a yellowish solid.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-OSSDKDCBOY-UHFFFADPSC-NUHFF-LREIQ-NUHFF-ZZZ

Christoph Schissler
1,2-Phenyl-5-(10,20-para-diethoxycarbonylphenylporphyrin-10,15,20-triphenylporphyrin) (1.0 mg, 0.8 µmol, 1.00 equiv.) and Cu(OAc)2 (1.2 mg, 6.6 µmol, 8.25 equiv.) were dissolved in a mixture of CHCl3 and MeOH (10:1, 2.1 mL). The reaction mixture was stirred for 1 h at 80 °C and the solvent was evaporated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ONZNTVWSXS-UHFFFADPSC-NUHFF-NBVCV-NUHFF-ZZZ

Christoph Schissler
Under an argon atmosphere 5,15-diphenylporphyrin (1.25 g, 2.70 mmol, 1.00 equiv.) was dissolved in dry THF (600 ml) and cooled down to 0 °C. Subsequently 1.9M Phenyllithium in buthylether (14 mL, 2.52 g, 25.9 mmol, 13.3 equiv.) was added. The reaction mixture was stirred at room temperature for 30 min and then quenched with water (3.5 mL). After stirring for 10 min, DDQ (650 mg, 2.86 mmol, 2.00 equiv.) was added and further stirred for...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ZRKUQAXOMU-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
4-Fluorobenzaldehyde (2.00 g, 1.73 mL, 16.1 mmol, 1.00 equiv), methanamine (40% in water, 1.88 g, 2.68 mL, 24.2 mmol, 1.50 equiv), tetrabutylammonium bromide (1.56 g, 4.83 mmol, 0.300 equiv) and potassium carbonate (2.23 g, 16.1 mmol, 1.00 equiv) were dissolved in DMSO (15.0 mL) and stirred at 95 °C for three days. Water was given to the reaction and the resulting mixture was extracted three times with ethyl acetate. The combined organic phases were washed...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-OOXACMCOHF-UHFFFADPSC-NUHFF-NIQCL-NUHFF-ZZZ

Christoph Schissler
1,2-Phenyl-(2-(5,10,15,20-tetraphenylporphyrin-10,15,20-triphenylporphyrin)-5-(10,15,20-triphenyporphyrin)) (0.3 mg, 0.24 µmol, 1.00 equiv.) and FeCl2 (0,7 mg, 5.52 µmol, 23.0 equiv.) were dissolved in DMF (0.5 mL). The reaction mixture was stirred for 14 h at 150 °C and the solvent evaporated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-DJGWMTKKMO-UHFFFADPSC-NUHFF-NNYHH-NUHFF-ZZZ

Stefan Marschner
To a solution of 933 mg of the porphyrin (1.54 mmol, 1.00 equiv.) in 385 mL CHCl3 were added 0.38 mL pyridine (377 mg, 4.77 mmol, 3.10 equiv.). The mixture was cooled to 0 °C and 646 mg NBS were added, as well as 50 mg in intervals of 30 min respectively, until a complete conversion was observed by TLC (∑ 746 mg, 4.19 mmol, 2.72 equiv.). After addition of the last portion, the reaction...

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