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

HRID 714094Notes

Reaction equation

HRID 714094 reaction equation
F[C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[C:19](=O)[CH2:18][CH2:17][C:16]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].FC(F)(F)C1C=CC(B(O)[OH:31])=CC=1>>[F:10][C:8]([F:9])([F:11])[C:7]1[CH:2]=[CH:3][C:4]([C:12]2[C:20]3[CH2:19][CH2:18][CH:17]([OH:31])[C:16]=3[CH:15]=[N:14][CH:13]=2)=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 898462774-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-[2]pyrindin-5-one

Product 1

HCID 71811532(rac)-4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-olYield 97%

Procedure

In analogy to the procedure described for the preparation of example 1 (rac)-4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol (intermediate A-4 [C2]) was reacted with 4-(trifluoromethyl)phenylboronic acid to give the title compound as grey solid in 97% yield. MS: 280.1 (M+H+).

Sources & evidence

ORD record
ord-07476b5cf5f34b959ed4b50201b26469
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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