Potassium Carbonate → 4-Chloro-5-(4-(trifluoromethyl)phenyl)-N-(3-hydroxyphenyl)isoxazole-3-carboxamide

HRID 1510440Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:17](Cl)=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[NH2:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[C:3]([C:17]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carbonyl chloride (15 mg, 0.05 mmol), 3-aminophenol (12.7 mg, 0.10 mmol) and potassium carbonate (7 mg, 0.05 mmol) in dichloromethane (8 mL) was heated to 45° C. overnight. The volatiles were removed in vacuo and the compound was purified by silica gel chromatography eluting with 3% methanol in dichloromethane to afford the title compound: (7.7 mg, 0.02 mmol). MS (ESI) m/z (M+H+): 383.1.

Workup

customThe volatiles were removed in vacuo
customthe compound was purified by silica gel chromatography
washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record: ord-601ea416e4af465e8f16fd453711c187
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211927B2

Reaction notes

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