5-Methyl-1,2-oxazole-4-carbonyl chloride → HCID 11739980, compound

HRID 1869289Notes

Reaction equation

[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([Br:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12](=[O:14])[CH3:13].[CH3:15][C:16]1[O:20][N:19]=[CH:18][C:17]=1[C:21](Cl)=[O:22]>O>[C:12]([C:3]1[O:4][C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=2[C:2]=1[NH:1][C:21]([C:17]1[CH:18]=[N:19][O:20][C:16]=1[CH3:15])=[O:22])(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 27 °C

Procedure

To a solution (10 ml) of 1-(3-amino-5-bromobenzofuran-2-yl)ethanone (0.2 g, 0.79 mmol) in water-free THF was added dropwise a solution (5 ml) of 5-methylisoxazole-4-carbonyl chloride (0.10 g, 0.79 mmol) in water-free THF under a nitrogen gas with vigorous stirring at 26-28° C. over 5 min. The reaction solution was heated at 65° C. for 2 hr. The reaction mixture was cooled to room temperature and the precipitate was collected by filtration. The precipitate was recrystallized from ethyl acetate to give N-(2-acetyl-5-bromobenzofuran-3-yl)-5-methylisoxazole-4-carboxamide as pale-yellow needle crystals (0.19 g, yield 68.0%).

Workup

temperatureThe reaction solution was heated at 65° C. for 2 hr
temperatureThe reaction mixture was cooled to room temperature
filtrationthe precipitate was collected by filtration
customThe precipitate was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-900457c554ca4472891ec6ab77c2efab
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638540B2

Reaction notes

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