Triethylamine → 5-Bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxamide

HRID 387299Notes

Reaction equation

C[N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[Br:30][C:31]1[CH:32]=[C:33]2[C:37](=[C:38]([C:40](O)=[O:41])[CH:39]=1)[NH:36][CH:35]=[C:34]2[CH2:43][CH:44]1[CH2:48][CH2:47][S:46](=[O:50])(=[O:49])[CH2:45]1.N.CO>ClCCl>[Br:30][C:31]1[CH:32]=[C:33]2[C:37](=[C:38]([C:40]([NH2:2])=[O:41])[CH:39]=1)[NH:36][CH:35]=[C:34]2[CH2:43][CH:44]1[CH2:48][CH2:47][S:46](=[O:50])(=[O:49])[CH2:45]1

Participants

Conditions

Temperature: 20 °C

Procedure

TBTU (5.68 g, 17.68 mmol) and triethylamine (1.79 g, 17.68 mmol) were added to a solution of 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylic acid (3.28 g, 8.84 mmol) in dichloromethane (100 mL). After the mixture was stirred for 0.5 h at 20° C., NH3/MeOH was added into the solution, and stirring continued for 2 h. The mixture was washed with water and extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum: ethyl acetate=10:1 to 5:1 to 2:1), giving 1.1 g (33.6%) of the title compound.

Workup

stirringstirring
waitcontinued for 2 h
washThe mixture was washed with water
extractionextracted with EtOAc
dry with materialThe organic phase was dried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography on silica gel (petroleum: ethyl acetate=10:1 to 5:1 to 2:1)

Sources & evidence

ORD record: ord-493861ac05414ce2abaf03139f036af2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372875B2

Reaction notes

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