Formic Acid → (r)-Cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

Participants

Reaction Steps

Combine (R)-cyclopropanecarboxylic acid[6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amide (Example 194) (3.70 g, 9.55 mmol) and nickel-aluminum catalyst (10.0 g) in 90% formic acid and heat at 90-100° C. for 18 h. Dilute with methanol, filter to remove catalyst, and concentrate the filtrate in vacuo. Neutralize the filtrate by addition of solid NaHCO3 after taking up in ethyl acetate/water. Dry the ethyl acetate portion over Na2SO4, filter, and evaporate to give 3.53 g (95%) of the title compound as a foam. MS (ES): n/z 391 (M+1); 1H NMR(DMSO-d6): δ 9.90 (s, 1H), 8.19 (d, 1H), 8.04 (s, 1H), 7.61 (d, 1H), 7.57 (d, 1H), 7.37 (dd, 1H), 7.15 (m, 1H), 6.81-6.92 (m, 2H), 5.44 (s, 2H), 4.08 (m, 1H), 3.03 (dd, 1H), 2.57-2.82 (m, 4H), 2.00 (m, 1H), 1.82 (m, 1H), 1.59 (m, 1H), 0.65 (m, 4H).

Provenance & Evidence