3-Fluoro-4-trifluoromethyl-phenylboronic acid → Racemic 4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol

HRID 714114Notes

Reaction equation

HRID 714114 reaction equation
Br[C:2]1[C:3]2[CH2:10][C:9]([CH3:12])([CH3:11])[CH:8]([OH:13])[C:4]=2[CH:5]=[N:6][CH:7]=1.[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22]>>[F:14][C:15]1[CH:16]=[C:17]([C:2]2[C:3]3[CH2:10][C:9]([CH3:12])([CH3:11])[CH:8]([OH:13])[C:4]=3[CH:5]=[N:6][CH:7]=2)[CH:18]=[CH:19][C:20]=1[C:21]([F:22])([F:23])[F:24]

Participants

3

Reactant 2

HCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 898459194-bromo-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol

Product 1

HCID 71811449Racemic 4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol

Procedure

In analogy to the procedure described for the preparation of examples 85 and 86, 4-bromo-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol (intermediate A-17) and 3-fluoro-4-trifluoromethyl-phenylboronic acid gave racemic 4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol. SFC separation afforded (+)-(7R)-4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol (example 108) and (−)-(7S)-4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]-pyridin-7-ol (example 109) as white solids. MS: 309.0 (M+H+).

Sources & evidence

ORD record
ord-a51ba288b2644f8095b0105cfb6dc38c
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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