4-(Trifluoromethyl)phenylboronic acid → N-((trans)-2-Hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1766462Notes

Reaction equation

HRID 1766462 reaction equation
Br[C:2]1[C:3]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[N:4][CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])=[O:8].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>>[OH:16][C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH:9][C:7](=[O:8])[C:6]1[CH:17]=[C:2]([C:28]2[CH:29]=[CH:30][C:25]([C:24]([F:35])([F:34])[F:23])=[CH:26][CH:27]=2)[C:3]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 675055315-Bromo-N-(trans-2-hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-nicotinamide

Product 1

HCID 11951478N-((trans)-2-Hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesised in analogy to the Suzuki reaction procedure described for the preparation of Example 1, from 5-bromo-N-(trans-2-hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-nicotinamide and 4-trifluoromethyl-phenylboronic acid (commercially available). MS (m/e): 439.3 (MH+).

Sources & evidence

ORD record
ord-6da1825c3a7a4a67914cb2647509edaf
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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