Ethyl Acetate → methyl 5-[4-(1-acetylazetidin-2-yl)phenyl]-6-chloro-1H-indole-3-carboxylate

참여 물질

역할	이름	HCID	투입량
반응물	Ethyl Acetate	HCID 8857	—
반응물	Potassium Carbonate	HCID 11430	—
반응물	methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate	HCID 86698665	—
반응물	1-(2-(4-Bromophenyl)azetidin-1-yl)ethanone	HCID 86698679	—
촉매	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
용매	Toluene ethanol	HCID 21863594	—
생성물	methyl 5-[4-(1-acetylazetidin-2-yl)phenyl]-6-chloro-1H-indole-3-carboxylate	HCID 86698680	51%

반응 조건

온도	110 °C

반응 단계

A mixture of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (100 mg, 0.311 mmol), 1-[2-(4-bromophenyl)azetidin-1-yl]ethanone (100 mg, 0.373 mmol), 2.0M aqueous potassium carbonate (0.50 mL, 1.0 mmol), and Pd(dppf)Cl2 (30 mg, 0.03 mmol) in toluene/ethanol (1.44 mL/0.48 mL) was stirred at 110° C. for 2.5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated to give a residue. This was purified by preparative TLC to give the title compound (40 mg, 51% yield) as a white solid.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08889730B2
출처 데이터셋	uspto-grants-2014_11
ORD ID	ord-e432a8eb1d904f02b8c4936ad933161c
출처 메모	uspto-grants-2014_11