4-(Trifluoromethoxy)phenylboronic acid → 6-Cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

HRID 1766464Notes

Reaction equation

HRID 1766464 reaction equation
Br[C:2]1[C:3]([O:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)=[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:36])([F:35])[O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>>[CH:20]1([CH2:19][O:18][C:3]2[C:2]([C:29]3[CH:28]=[CH:27][C:26]([O:25][C:24]([F:23])([F:35])[F:36])=[CH:31][CH:30]=3)=[CH:17][C:6]([C:7]([NH:9][C@@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[OH:16])=[O:8])=[CH:5][N:4]=2)[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 675049715-bromo-6-cyclopropylmethoxy-N-(trans-2-hydroxy-cyclohexyl)-nicotinamide

Product 1

HCID 119516576-Cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 23, using 5-bromo-6-cyclopropylmethoxy-N-(trans-2-hydroxy-cyclohexyl)-nicotinamide and 4-trifluoromethoxyphenylboronic acid (commercially available) as starting materials. MS (m/e): 451.3 (MH+).

Workup

  1. customdescribed for the preparation of Example 23

Sources & evidence

ORD record
ord-e2376343ac6f49b789fe48bd03cadc92
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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