Ethyl orthoformate → tert-butyl [4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

Participants

Reaction Steps

To a solution of tert-butyl (6-amino-4-ethylpyridin-3-yl)acetate (198 mg, 0.838 mmol) in EtOAc (4 mL) was added trimethylsilyl trifluoroacetate (0.246 ml, 1.424 mmol) at room temperature. After stirred 5 min, triethyl orthoformate (0.251 ml, 1.508 mmol) was added. After stirred another 5 min, azidotrimethylsilane (0.176 ml, 1.34 mmol) was added. The reaction mixture was stirred at RT for two days, then concentrated. The residue was purified prep TLC (hex/EA=1/1) to give title compound. LC-MS: [(M+1)]+=290.23, [(M+1-28)]+=262.22, [(M+1-28-56)]+=206.21

Provenance & Evidence