Acetic Acid → HCID 25260942, compound

Participants

Reaction Steps

To a solution of 3-(2-Phenyl-pyridin-4-yl)-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-imidazo[1,2-a]pyridine (Ex. 1.190) (1.0 eq, 0.2 mmol, 90 mg) in MeOH (2 ml) is added acetone (10 eq, 1.04, 0.76 ml) and acetic acid (2 eq, 0.21 mmol, 0.1 ml) and the reaction mixture is stirred at room temperature for 30 min. After this time sodium triacetoxyborohydride (5 eq, 0.52 mmol, 116 mg) is added to the reaction mixture and is stirred for a further 2 h. The reaction is diluted with CH2Cl2 and the organic phase is washed with NaHCO3. The aqueous layer is further extracted with EtOAc. The combined organic layers are washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 8:2 DCM/MeOH to yield 7-(1-isopropyl-1,2,3,6-tetrahydro-pyridin-4-yl)-3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridine as a light yellow solid; [M+H]+=395

Provenance & Evidence