Acetic Acid → HCID 25261430, compound

Participants

Reaction Steps

To a solution of 3-[3-(2-isopropylamino-6-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-benzaldehyde (Ex. 1.186) (1 eq, 0.055 mmol, 30 mg) in MeOH (2 ml) is added ethyl amine (10 eq, 0.55, 0.27 ml) and acetic acid (2 eq, 0.11 mmol, 6.59 mg) and the reaction mixture is stirred at room temperature for 30 min. After this time sodium triacetoxyborohydride (5 eq, 0.27 mmol, 58.2 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 {4-[7-(3-ethylaminomethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-6-phenyl-pyridin-2-yl}-isopropyl-amine as a light yellow solid; [M+H]+=462

Provenance & Evidence