Dichloromethane → HCID 89748357, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (197, 1.95 g, 6.32 mmol), 4-bromo-2fluoroaniline (1.00 g, 5.26 mmol), Pd(dppf)Cl2.DCM (0.43 g, 0.526 mmol), K2CO3 (1.45 g, 10.5 mmol) were mixed in 40 mL dioxane and 20 mL water. The mixture was degassed with N2 stream for 3 min and stirred at 90° C. in N2 atmosphere for overnight. The mixture was cooled to RT, concentrated in vacuo, diluted with 120 mL EtOAc, washed with water ×2, dried, concentrated, and subjected to silica flash column to isolate tert-butyl 4-(4-amino-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (198, 1.55 g, quantitative yield) using 0 to 25% EtOAc in hexane. It was dissolved in 150 mL iPrOH, and to it was hydrogenated with 10% Pd/C using a balloon for overnight. The mixture was filtered through celite, concentrated in vacuo to afford tert-butyl 4-(4-amino-3-fluorophenyl)piperidine-1-carboxylate (199) in quantitative yield.

Provenance & Evidence