Potassium Phosphate, Tribasic → 7-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide

関与物質

役割	名称	HCID	仕込み量
反応物	Potassium Phosphate, Tribasic	HCID 62657	—
反応物	3-Difluoromethyl-phenylboronic acid	HCID 44717244	—
反応物	[2-(7-Bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester	HCID 58816140	—
触媒	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
溶媒	Water	HCID 962	—
溶媒	Dimethoxyethane methanol	HCID 86595564	—
生成物	7-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide	HCID 11280346	88.3%

反応条件

温度	82 °C

反応手順

Dissolve [2-(7-bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (0.13 g, 0.30 mmol) and 3-(difluoromethyl)phenylboronic acid (0.057 g, 0.33 mmol) in DME-methanol (8:1, 10 ml). To the mixture, add K3PO4 (0.13 g, 0.60 mmol), and PdCl2(dppf) (0.012 g, 0.015 mmol). Heat this mixture at 82° C. overnight. Cool the reaction mixture, dilute with water and extract with EtOAc. Wash with brine and evaporate to dryness. Purify by silica gel chromatography to give the desired compound (0.10 g, 71% yield): 1H NMR (CDCl3): δ9.39 (s, 1H), 8.66 (m, 2H), 8.43 (d, J=5.7 Hz, 2H), 7.86 (m, 2H), 7.61 (m, 2H), 6.76 (t, J=52.1 Hz, 1H), 5.00 (br s, 1H), 3.18 (m, 2H), 3.03 (m, 2H), 1.37 (s, 9H); ESIMS: m/z 478 (M+H)+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07449477B2
出典データセット	uspto-grants-2008_11
ORD ID	ord-1c02f53ad4f34396a0e03e34fad62472
出典メモ	uspto-grants-2008_11