Diisopropylethylamine → N-(2-(5-bromo-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylethylamine	HCID 81531	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
反応物	2-(5-bromo-1H-indol-3-yl)ethan-1-amine hydrochloride	HCID 13241175	—
反応物	5-(2,5-Difluorobenzyl)isoxazole-3-carboxylic acid	HCID 66832039	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	N-(2-(5-bromo-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide	HCID 66831747	60%

反応手順

A solution of 5-(2,5-difluorobenzyl)isoxazole-3-carboxylic acid (0.104 g, 0.435 mmol), 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride (0.120 g; 0.435 mmol), HATU (0.166 g; 0.435 mmol) and N,N diisopropylethylamine (0.201 mL; 1.09 mmol) in DMF (5 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.120 g (60%) of N-(2-(5-bromo-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide as a white solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09434722B2
出典データセット	uspto-grants-2016_09
ORD ID	ord-a2a76de4b97e40f8822b491bcf600dd0
出典メモ	uspto-grants-2016_09