Triethylamine → methyl 5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-methyl-5-(tributylstannyl)-1H-1,2,3-triazole	HCID 22609826	—
Reactant	Methyl 4-bromo-5-chlorothiophene-2-carboxylate	HCID 57826388	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Toluene	HCID 1140	—
Product	methyl 5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylate	HCID 57826646	32%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of 1-methyl-5-(tributylstannanyl)-1H-1,2,3-triazole (2.0 g, 5.37 mmol), methyl 4-bromo-5-chloro-2-thiophenecarboxylate (1.25 g, 4.9 mmol), Pd(PPh3)2Cl2 (171 mg, 0.244 mmol), TRIETHYLAMINE (0.68 ml, 4.89 mmol) and toluene (3 ml) was heated at 110° C. for 4 hr under N2. The reaction mixture was purified via column chromatography (silica, 50%-70% EtOAc in hexane) to give the title compound as a white solid (400 mg, 32%): LCMS (ES) m/z 258.2 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08273782B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-71f26ab2cfd6422b95e03807d8a7f8c6
Source note	uspto-grants-2012_09