Water → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

関与物質

役割	名称	HCID	仕込み量
反応物	Water	HCID 962	—
反応物	3-Methoxypropyne	HCID 69393	—
反応物	2-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one	HCID 59790307	—
触媒	Tetrakis(triphenylphosphine)palladium	HCID 11979704	—
溶媒	Pyrrolidine	HCID 31268	—
生成物	2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one	HCID 57435886	63%

反応条件

温度	80 °C

反応手順

A solution of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (0.65 g, 1.6 mmol) in pyrrolidine was treated with 3-methoxy-propyne (0.27 mL, 3.2 mmol) followed by tetrakis(triphenylphosphine) palladium(0) (90 mg, 0.08 mmole), heated to 80° C. for 4 hrs, poured into water and extracted with ethyl acetate. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography on silica gel in ethyl acetate to give the title product as a brown wax, 0.4 g (63% yield), identified by NMR and mass spectral analyses.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07423158B2
出典データセット	uspto-grants-2008_09
ORD ID	ord-c3329fbe5df146018136ee8d5ed1fb17
出典メモ	uspto-grants-2008_09