Methyl iodide → HCID 71515783, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 10: To a solution of 3-[5-acetyl-1-((1R,2R)-4,6-difluoro-2-hydroxy-indan-1-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (11t) (0.10 g, 0.276 mmol) in dry DMF (1 ml) at −10° C. NaHMDS (50 mg) was added. After 5 min iodomethane (39 mg, 0.276 mmol) was added and the mixture was allowed to warm to 25° C. After 90 min the mixture was cooled to −10° C. and the same amount of both NaHMDS and iodomethane was added again. After stirring overnight the mixture was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 27 mg of 3-[5-acetyl-1-((1R,2R)-4,6-difluoro-2-methoxy-indan-1-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (16a). Rt=1.29 min (LC method 4). Detected mass: 449.32 [M+H+]

Provenance & Evidence