Aniline → 3-(4-Methyl-3-oxo-7-phenylamino-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/519109

関与物質

役割	名称	HCID	仕込み量
反応物	Aniline	HCID 6115	—
反応物	Cesium carbonate	HCID 10796	—
反応物	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
反応物	3-(7-Bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester	HCID 86727293	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	3-(4-Methyl-3-oxo-7-phenylamino-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester	HCID 86727488	14%

反応手順

A solution of 3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (Example #1, Step B, 0.1 g, 0.21 mmol), aniline (0.06 g, 0.64 mmol), Pd2(dba)3 (0.039 g, 0.04 mmol), Xantphos (0.0496 g, 0.09 mmol), and Cs2CO3 (0.14 g, 0.43 mmol) in anhydrous dioxane (10 mL) was heated at 130° C. for 14 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo, The residue was purified by chromatography on silica gel (eluting with 50% EtOAc in petroleum ether) to give 3-(4-methyl-3-oxo-7-phenylamino-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.014 g, 14%) as brown solid. LC/MS (Table 1, Method 2) Rt=1.205 min; MS m/z: 542 [M+23+41]+

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09115151B2
出典データセット	uspto-grants-2015_08
ORD ID	ord-e351f5ce8d4b4645969edc2f11bd03a5
出典メモ	uspto-grants-2015_08