Acetic Acid → 3-{3-[(1-oxo-1,2,3,7,8,9-hexahydropyrano[3,2-e]isoindol-8-yl)amino]propyl}-1H-indole-5-carbonitrile

Participants

Reaction Steps

To a mixture of (1) (60 mg, 0.294 mmol), 4-(5-fluoro-1H-indol-3-yl)butanal (21), 64 mg, 0.309 mmol) in acetic acid (37 μl, 0.62 mmol) and methanol (2 ml) was added NaBH3CN (37 mg, 0.59 mmol) in portions. Resulting mixture was stirred for 1.5 hr. The solvent was removed in vacuo and the residue was dissolved in CH2Cl2 and washed with 1 N NaOH and saturated NaCl. The organic solution was dried over Na2SO4 and concentrated in vacuo. The compound was purified on silica gel eluting with 60% EtOAc/Hexane to give (20) as a solid (78 mg, 69%). The title compound was dissolved in methylene chloride and treated with 1 equivalent of etherate HCl to give HCl salt. MS (ES) m/z 385.2.

Provenance & Evidence