2-Amino-4-difluoromethyl-5-iodo-benzoic acid methyl ester → 2-Amino-4-difluoromethyl-5-(2-isopropyl-2H-pyrazol-3-yl)-benzoic acid methyl ester

참여 물질

역할	이름	HCID	투입량
반응물	2-Amino-4-difluoromethyl-5-iodo-benzoic acid methyl ester	HCID 59164445	—
반응물	1-Isopropyl-5-tributylstannanyl-1H-pyrazole	HCID 59164521	—
촉매	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
용매	1,4-Dioxane	HCID 31275	—
생성물	2-Amino-4-difluoromethyl-5-(2-isopropyl-2H-pyrazol-3-yl)-benzoic acid methyl ester	HCID 59164477	54%

반응 조건

온도	90 °C

반응 단계

To a solution of 2-amino-4-difluoromethyl-5-iodo-benzoic acid methyl ester (750 mg, 2.29 mmol) in dioxane (30 mL) were added 1-isopropyl-5-tributylstannanyl-1H-pyrazole (1.1 g, 1.2 equiv) and Pd(dppf)2Cl2 (187 mg, 0.1 equiv) and the resulting mixture was stirred at 90° C. for 18 h. Another portion of catalyst (0.1 equiv) was added and the mixture was stirred at 90° C. for an additional 6 h. The solvent was removed in vacuo to afford a dark oil. The crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 30:70)) to provide the title compound as an off-white solid (380 mg, 54%). ES-MS: m/z 310.3 [M+H]+, rt 5.54 min.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08012988B2
출처 데이터셋	uspto-grants-2011_09
ORD ID	ord-d4a233ee4c5146daba7256badbfc6a64
출처 메모	uspto-grants-2011_09