Water → 4-(6-Amino-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (198.7 mg, 0.3841 mmol), 4-boronobenzoic acid (63.74 mg, 0.3841 mmol) and Na2CO3 (81.42 mg, 0.7682 mmol) was suspended in MeCN (3.213 mL)/water (3.213 mL) and degassed (nitrogen/vacuum cycles). The reaction was then treated with tetrakis(triphenylphosphine)palladium(0) (44.39 mg, 0.03841 mmol), degassed again and heated at 110° C. in the microwave for 30 minutes. The reaction was treated with water (0.5 mL) and heated in the microwave at 110° C. for a further 30 minutes. The reaction mixture was washed with DCM, the aqueous phase acidified to pH1 (by addition of 1M HCl), and resulting precipitate filtered off and washed with water to give the product as an orange solid (75 mg, 55% Yield). MS (ES+) 359.14.

Provenance & Evidence