Potassium Phosphate, Tribasic → HCID 67959857, compound

Participants

Reaction Conditions

Reaction Steps

A brown solution of (4R)-tert-butyl 4-(6-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (469.5 mg, 0.803 mmol), 4,4,6-trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)1,3,2-dioxaborinane (Frontier Scientific, Inc., Logan, Utah; 0.250 mL, 1.205 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (Xphos; Strem, Newburyport, Mass.; 38.3 mg, 0.080 mmol), Pd2(dba)3 (36.8 mg, 0.040 mmol), and potassium phosphate (853 mg, 4.02 mmol) in a mixture of dioxane (7.0 mL) and water (0.700 mL) was stirred under argon at 95° C. for 1.5 h. The reaction was cooled to RT, concentrated onto silica gel, and chromatographically purified (ISCO, 40 g silica gel column, 0-50% EtOAc/hexanes, 15 min, 254 nm) to provide (4R)-tert-butyl 4-(6-(1-(tetrahydro-2H-pyran-2-yl)-5-(3,3,3-trifluoroprop-1-en-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (438.7 mg, 0.732 mmol, 91% yield) as a white foam: MS (ESI, pos. ion) m/z: 600.3 (M+1).

Provenance & Evidence