Potassium Carbonate → (E)-tert-butyl 3-((8-(2-ethoxyvinyl)-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate

https://huagongshe.com/reaction/519062

関与物質

役割	名称	HCID	仕込み量
反応物	Potassium Carbonate	HCID 11430	—
反応物	1-Ethoxyethene-2-boronic acid pinacol ester	HCID 21973908	—
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	HCID 178418807	HCID 178418807	—
溶媒	Water	HCID 962	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	(E)-tert-butyl 3-((8-(2-ethoxyvinyl)-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate	HCID 86727429	51%

反応条件

温度	100 °C

反応手順

To a solution of tert-butyl 3-((8-bromo-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate (Example 1, Step B, 0.20 g, 0.43 mmol), (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.1 g, 0.5 mmol) in dioxane (6 mL) and water (1 mL) was added PdCl2(dppf)-CH2Cl2 adduct (0.035 g, 0.043 mmol) and K2CO3 (0.118 g, 0.85 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to ambient temperature, the solvent was removed in vacuo and the residue was purified by chromatography on silica gel (eluting with 2% MeOH in DCM) to give (E)-tert-butyl 3-((8-(2-ethoxyvinyl)-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate (0.10 g, 51%) as a yellow solid. LC/MS (Table 1, Method 2) Rt=1.352 min.; MS m/z: 458 [M+H]+.

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-4eec6d78a3054aa0ba84a9e27bf51d06
出典メモ	uspto-grants-2015_08