3-Fluoro-4-trifluoromethyl-phenylboronic acid → 4-[3-Fluoro-4-(trifluoromethyl)phenyl]-6,7-dihydro-5H-cyclopenta[c]pyridine-7-ol

HRID 714093Notes

Reaction equation

HRID 714093 reaction equation
[F:1][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].FC1C=C(B(O)[OH:34])C=CC=1C(F)(F)F>>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[CH2:19][CH2:18][CH:17]([OH:34])[C:16]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:9])[F:11]

Participants

3

Reactant 2

HCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 898462774-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-[2]pyrindin-5-one

Product 1

HCID 718115334-[3-Fluoro-4-(trifluoromethyl)phenyl]-6,7-dihydro-5H-cyclopenta[c]pyridine-7-olYield 55%

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 3-fluoro-4-(trifluoromethyl)phenylboronic acid to give the title compound as grey solid in 55% yield. MS: 298.1 (M+H+).

Sources & evidence

ORD record
ord-0fddc5271ab4475fa35782358049085a
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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