2-methylidenepiperidine

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methylene piperidine ED.8 (243 mg, 1.23 mmol) is combined with 9-BBN (2.46 mL, 0.5 M in THF) and heated to 65° C. for 1 h. Then the mixture is cooled to 20° C., quinoxaline D*.5 (300 mg, 1.23 mmol), Pd(dppf) (50 mg, 10 mol %) and K2CO3 (195 mg, 1.41 mmol) are placed in DMF/H2O (1.2 mL, 5:1) and slowly the freshly prepared boronate is added dropwise. The reaction mixture is heated to 60° C. for 2 h, cooled, combined with NaHCO3 and extracted with DCM (3×10 mL). The solvent is removed, the residue is purified by chromatography (45:55 to 90:10 in 6 min CH3CN/H2O) and quinoxaline D.51 (250 mg, 50%) is obtained. Then the mixture is cooled to 20° C. The reaction mixture is heated to 60° C. for 2 h cooled extracted with DCM (3×10 mL) The solvent is removed the residue is purified by chromatography (45:55 to 90:10 in 6 min CH3CN/H2O) and quinoxaline D.51 (250 mg, 50%) is obtained