Potassium Phosphate, Tribasic → HCID 58293789, compound

Participants

Reaction Conditions

Reaction Steps

N-tert-Butyl-3-(1-(4-bromo-2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine (Compound 1080 150 mg, 0.366 mmol), potassium cyclopropyltrifluoroborate (70.5 mg, 0.476 mmol), tricyclohexylphosphine (10 mg, 0.0366 mmol) and K3PO4 (272 mg, 1.283 mmol) were taken into toluene (1.5 ml), and water (750 μL). The reaction was degassed with nitrogen for 1 hour and Pd(OAc)2 (4.1 mg, 0.0183 mmol) was added. The reaction mixture was heated at 180° C. for 10 minutes under microwave irradiation. The reaction was found to be incomplete by HPLC analysis so tetrakis-(triphenylphosphine) palladium (0) (42 mg, 0.0366 mmol) was added to the mixture and microwave irradiation was continued for 10 minutes at 180° C. The reaction mixture was poured in water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and the volatiles removed under reduced pressure to afford a crude brown oil, which was purified by column chromatography (SiO2), eluting with 0-20% EtOAc/hexanes, to afford 120 mg of N-tert-butyl-3-(1-(4-cyclopropyl-2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine (Compound 1084) as a colorless oil; ESMS (M+1)=371.

Provenance & Evidence