2-Fluoro-4-(trifluoromethyl)benzeneboronic acid → (rac)-N-(4-(2-Fluoro-4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 714084Notes

Reaction equation

HRID 714084 reaction equation
Br[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=2[CH:5]=[N:6][CH:7]=1.[F:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1B(O)O>>[F:16][C:17]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:18]=1[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 164141452-Fluoro-4-(trifluoromethyl)benzeneboronic acidHCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

Product 1

HCID 71811609(rac)-N-(4-(2-Fluoro-4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideYield 76%

Procedure

In analogy to the procedure described for the preparation of example 1, (rac)-N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide (intermediate A-4) was reacted with 2-fluoro-4-(trifluoromethyl)phenylboronic acid to give the title compound as grey solid in 76% yield. MS: 353.1 (M+H+).

Sources & evidence

ORD record
ord-75f122b796654e6da7cf2773043860cd
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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