1-benzyloxy-5-tributylstannanyl-1H-pyrazole → HCID 59164449, compound

Participants

Role	Name	HCID	Charge
Reactant	1-benzyloxy-5-tributylstannanyl-1H-pyrazole	HCID 10479501	—
Reactant	Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate	HCID 53436880	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 59164449	HCID 59164449	31%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 2-amino-4-trifluoromethyl-5-iodo-benzoic acid methyl ester (750 mg, 2.17 mmol) in dioxane (15 mL) were added 1-benzyloxy-5-tributylstannanyl-1H-pyrazole (1.24 g, 2.60 mmol) and Pd(dppf)2Cl2 (177 mg, 0.217 mmol) and the resulting mixture was stirred at 100° C. for 16 h. An additional portion of catalyst (0.1 equiv) was added and the mixture was stirred at 100° C. for an additional 24 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 50:50)) to provide the title compound as an off-white solid (263 mg, 31%). ES-MS: m/z 392.3 [M+H]+, rt 6.48 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07655666B2
Source dataset	uspto-grants-2010_02
ORD ID	ord-2d8be9d6dbe94465ae0d4fcce0050c6c
Source note	uspto-grants-2010_02