2-Methoxyethanol → (RS)-5-(4-chloro-phenyl)-6-(2-methoxy-ethoxy)-N-(3,3,3-trifluoro-2-hydroxy-propyl)-nicotinamide

HRID 1766465Notes

Reaction equation

HRID 1766465 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7]([OH:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[NH2:23][CH2:24][CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27].[CH3:31][O:32][CH2:33][CH2:34]O>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:8]2[C:7]([O:11][CH2:34][CH2:33][O:32][CH3:31])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:23][CH2:24][CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27])=[O:12])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 742994-Chlorophenylboronic acidHCID 4189653-Amino-1,1,1-trifluoropropan-2-olHCID 2764315Methyl 5-bromo-6-hydroxynicotinate

Product 1

HCID 11951660(RS)-5-(4-chloro-phenyl)-6-(2-methoxy-ethoxy)-N-(3,3,3-trifluoro-2-hydroxy-propyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 102, using 5-bromo-6-hydroxy-nicotinic acid methyl ester, 2-methoxyethanol, (4-chloro-phenyl)-boronic acid and 3-amino-1,1,1-trifluoro-propan-2-ol (CAS [431-38-9]) as starting materials to yield (RS)-5-(4-chloro-phenyl)-6-(2-methoxy-ethoxy)-N-(3,3,3-trifluoro-2-hydroxy-propyl)-nicotinamide. MS (ISP) 419.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 102

Sources & evidence

ORD record
ord-8ec38be207bc4663888feb629d7a5e8a
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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