2-Aminocyclohexanol → 2-[3-(2-Methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol

Participants

Reaction Steps

6-Chloro-3-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine (Intermediate G) (1 eq, 200 mg, 0.769 mmol), sodium tert-butoxide (2.4 eq, 1.8 mmol, 177 mg), palladium acetate (17 mg, 0.1 eq), (R)-1-[(1S)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine (43 mg, 0.1 eq) are stirred at RT under an inert atmosphere of argon in DME (3 ml) and degassed thoroughly before adding 2-aminocyclohexanol (2 eq, 1.53 mmol, 176 mg) The reaction is heated using microwave radiation at 100° C. for 2 hours. The majority of the solvent is removed in vacuo and the resulting residue is loaded onto a SCX-2 cartridge (resin loading 0.67 mmol/g) eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and further purified by flash chromatography (10% MeOH/EtOAc) to afford the title compound; [M+H]+=339

Provenance & Evidence