1-methyl-5-(tributylstannyl)-1H-1,2,3-triazole → 2-Amino-5-(3-methyl-3H-[1,2,3]triazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	1-methyl-5-(tributylstannyl)-1H-1,2,3-triazole	HCID 22609826	—
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	2-Amino-5-(3-methyl-3H-[1,2,3]triazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester	HCID 59164436	41%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 2-amino-4-trifluoromethyl-5-iodo-benzoic acid methyl ester (1 g, 2.90 mmol) in dioxane (20 mL) were added 1-methyl-5-tributylstannanyl-1H-[1,2,3]triazole (2.02 g, 4.34 mmol) and Pd(dppf)2Cl2 (237 mg, 0.29 mmol) and the resulting mixture was stirred at 100° C. for 24 h. A portion of catalyst (0.1 equiv) was added and the mixture was stirred at 100° C. for an additional 7 h. The solvent was removed in vacuo to afford a dark oil. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes (0:1000 to 40:60)) to provide the title compound as an off-white solid (357 mg, 41% yield). ES-MS: m/z 301.2 [M+H]+, rt 4.49 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08513268B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-b32c4a14e0eb46cabe996e56e5236036
Source note	uspto-grants-2013_08