3-(Trifluoromethyl)phenylboronic acid → N-[1-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]-5-[3-(trifluoromethyl)phenyl]pyridine-2-carboxamide

HRID 876292Notes

Reaction equation

HRID 876292 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:25]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[CH2:12]2)=[O:9])=[N:6][CH:7]=1.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1>>[CH:27]1([C:25]([N:13]2[CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=3)[CH2:16][CH:11]([NH:10][C:8]([C:5]3[CH:4]=[CH:3][C:2]([C:38]4[CH:37]=[CH:36][CH:35]=[C:34]([C:33]([F:44])([F:43])[F:32])[CH:39]=4)=[CH:7][N:6]=3)=[O:9])[CH2:12]2)=[O:26])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 667615095-Bromo-N-[1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]pyridine-2-carboxamide

Product 1

HCID 46931634N-[1-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]-5-[3-(trifluoromethyl)phenyl]pyridine-2-carboxamide

Procedure

59 mg (0.12 mmol) of 5-bromo-N-[1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]pyridine-2-carboxamide (Example 82) and 27 mg (0.14 mmol, 1.2 eq.) of [3-(trifluoromethyl)phenyl]boronic acid were reacted according to General Method 7. Yield: 46 mg (71% of theory)

Sources & evidence

ORD record
ord-a8a170ac85cd45d183e955c35984cdd0
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

Loading…