Ammonium formate → HCID 59508043, compound

Participants

Reaction Conditions

Reaction Steps

3-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-(2-methoxy-pyridin-3-yl)-1H-indole (0.53 g, 1.34 mmol), 10% Pd/C (50 mg), and ammonium formate (0.85 g, 13.4 mmol) were combined in methanol (100 ml) and heated at 60° C. for 2 h. The reaction was cooled, filtered through celite, and the filter cake washed with methanol. The solvent was removed under reduced pressure to give the desired product as a yellow foamy solid (0.56 g, qunatitative) which could be used in the next reaction without any further purification or purified by reverse phase chromatography. M.p.=110-115° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.11 (s, 1H, indole-NH), 8.58 (brs, 1H, NHHCl), 8.48 (brs, 1H, NHHCl), 8.26 (dd, J1=2.0 Hz, J2=4.8 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.75 (dd, J1=2.0 Hz, J2=7.6 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.14 (dd, J1=5.2 Hz, J2=7.6 Hz, 1H), 7.10 (m, 1H), 7.00 (m, 1H), 3.94 (s, 3H), 3.37 (m, 2H), 2.96 (m, 2H), 2.83 (m, 1H), 2.34 (m, 2H), 1.82 (m, 2H); LCMS: 308.65 [M+H].

Provenance & Evidence