HCID 59164470, compound → HCID 59164455, compound

Participants

Role	Name	HCID	Charge
Reactant	HCID 59164470	HCID 59164470	—
Reactant	1-Isopropyl-5-tributylstannanyl-1H-pyrazole	HCID 59164521	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 59164455	HCID 59164455	40%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 2-amino-4-fluoromethyl-5-iodo-benzoic acid methyl ester (650 mg, 2.10 mmol) in dioxane (30 mL) were added 1-isopropyl-5-tributylstannanyl-1H-pyrazole (1.01 g, 1.2 equiv) and Pd(dppf)2Cl2 (172 mg, 0.1 equiv) and the resulting mixture was stirred at 90° C. for 18 h. 0.1 equiv of catalyst was added and the mixture was stirred at 90° C. for 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 35:75)) to provide a light yellow solid (243 mg, 40%) (ES-MS: m/z 292.3 [M+H]+, rt 5.31 min).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08513268B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-24c016fcbe3a46f58fa11b19ea2ef5cd
Source note	uspto-grants-2013_08