4-(Trifluoromethyl)phenylboronic acid → (rac)-N-(4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 714081Notes

Reaction equation

HRID 714081 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]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:3]3[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=3[CH:5]=[N:6][CH:7]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

Product 1

HCID 71811647(rac)-N-(4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideYield 87%

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 4-(trifluoromethyl)phenylboronic acid to give the title compound as grey solid in 87% yield. MS: 335.1 (M+H+).

Sources & evidence

ORD record
ord-e5ea7d9534ac4a439ee751a74f447218
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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