2,2,2-Trifluoroethanol → 5-(4-Chloro-phenyl)-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide

HRID 1159256Notes

Reaction equation

HRID 1159256 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[F:13][C:14]([F:18])([F:17])[CH2:15][OH:16].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[NH2:29][CH2:30][C:31]([CH:34]1[CH2:36][CH2:35]1)([OH:33])[CH3:32]>>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:8]2[C:7]([O:16][CH2:15][C:14]([F:18])([F:17])[F:13])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:29][CH2:30][C:31]([CH:34]2[CH2:36][CH2:35]2)([OH:33])[CH3:32])=[O:12])=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 742994-Chlorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 211096921-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 119523845-(4-Chloro-phenyl)-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 5, using 5-bromo-6-chloro-nicotinic acid methylester, 2,2,2-trifluoro-ethanol (commercially available), 4-chlorophenyl-boronic acid (commercially available) and rac-1-amino-2-cyclopropyl-propan-2-ol (commercially available) as starting materials. MS (ISP): 429.1 (M+H+).

Workup

  1. customdescribed for the preparation of Example 5

Sources & evidence

ORD record
ord-b6ec4ad3940c40bbae2fb2e2e8e76651
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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