4-(Trifluoromethyl)phenylboronic acid → (rac)-7-Methyl-4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol

HRID 714095Notes

Reaction equation

HRID 714095 reaction equation
Br[C:2]1[C:3]2[CH2:10][CH2:9][C:8]([CH3:12])([OH:11])[C:4]=2[CH:5]=[N:6][CH:7]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[CH3:12][C:8]1([OH:11])[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:18]3[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=3)[C:3]=2[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 898463494-Bromo-7-methyl-6,7-dihydro-5H-cyclopenta[C]pyridin-7-OL

Product 1

HCID 71760914(rac)-7-Methyl-4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-olYield 85%

Procedure

In analogy to the procedure described for the preparation of example 1 (rac)-4-bromo-7-methyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol (intermediate A-13) was reacted with 4-(trifluoromethyl)phenylboronic acid to give the title compound as grey solid in 85% yield. MS: 294.1 (M+H+)

Sources & evidence

ORD record
ord-7ae263d45c8f4505bae8462e6aa9a88d
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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