(3-Propoxyphenyl)boronic acid → 2-(3-Propoxy-phenyl)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

HRID 2363163Notes

Reaction equation

HRID 2363163 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21](Cl)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[CH2:25]([O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)[CH2:26][CH3:27]>>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([O:28][CH2:25][CH2:26][CH3:27])[CH:34]=3)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 3691230(3-Propoxyphenyl)boronic acidHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 672393462-(3-Propoxy-phenyl)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amideYield 16%

Procedure

2-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.13 mmol) was reacted with 3-propoxy phenyl boronic acid (47 mg, 0.26 mmol) to give the title compound (10 mg, 16%) after purification by column chromatography (gradient 12% to 100% EtOAc in n-hexane).

Sources & evidence

ORD record
ord-ca4047c131994d78be06f2f73f960fac
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

Loading…