3-Fluoro-4-trifluoromethyl-phenylboronic acid → (rac)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamide

HRID 714086Notes

Reaction equation

HRID 714086 reaction equation
Br[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:4]=2[CH:5]=[N:6][CH:7]=1.[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25]>>[F:17][C:18]1[CH:19]=[C:20]([C:2]2[C:3]3[CH2:10][CH2:9][CH:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:4]=3[CH:5]=[N:6][CH:7]=2)[CH:21]=[CH:22][C:23]=1[C:24]([F:25])([F:26])[F:27]

Participants

3

Reactant 2

HCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 89456129N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamide

Product 1

HCID 71811603(rac)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamideYield 72%

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)ethanesulfonamide (intermediate A-7) was reacted with 3-fluoro-4-(trifluoromethyl)phenylboronic acid to give the title compound as off-white solid in 72% yield. MS: 389.1 (M+H+).

Sources & evidence

ORD record
ord-7d527efbd4a84112acabb3632c9260ed
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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