1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate → 1,1-Dimethylethyl N-((7-cyano-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate

関与物質

役割	名称	HCID	仕込み量
反応物	1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate	HCID 67099764	—
反応物	HCID 178418260	HCID 178418260	—
触媒	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
触媒	Tetraethylammonium cyanide	HCID 3014735	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	1,1-Dimethylethyl N-((7-cyano-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate	HCID 67099761	60.2%

反応条件

温度	75 °C

反応手順

1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (310 mg, 731 μmol, see Example 53), dppf (162 mg, 292 μmol), tris(dibenzylideneacetone)dipalladium (66.9 mg, 73.1 μmol), copper cyanide (262 mg, 2923 μmol), and tetraethylammonium cyanide (126 mg, 804 μmol) were mixed in dioxane (6 mL) in a microwave tube under a nitrogen atmosphere. The reaction mixture was then stirred at 75° C. for 16 hours. The reaction mixture was returned to room temperature, fused to silica gel, and purified by silica flash chromatography (0-100% DCM/hexane) to give the desired ester as a white solid (163 mg). MS (m/e)=315.1 (M+H-tBu)+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07635715B2
出典データセット	uspto-grants-2009_12
ORD ID	ord-446a6c1ad3f54af18f412f15c94e7d15
出典メモ	uspto-grants-2009_12