Potassium Carbonate → Ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (24g) (300 mg, 1.11 mmol) in DMF (9 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (414 mg, 1.34 mmol), K2CO3 (1.8M, 1.85 mL, 3.33 mmol) and Pd(PPh3)4(87 mg, 0.11 mmol). The reaction was evacuated and backfilled with nitrogen twice then heated at 160° C. for 10 minutes via microwave. After the reaction mixture was filtered through a pad of Celite, the mixture was diluted with a saturated solution of NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give crude ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (89) (MS (m/z) 372.1 (M+1)+.

Provenance & Evidence