HCID 57431646, compound → HCID 59161195, compound

Participants

Reaction Steps

Add sulfided platinum (5 wt % on carbon) (120 mg) to a solution of N-[6-cyano-9-(3-nitro-benzyl)2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 88) (470 mg, 1.1 mmol) and methanol (50 mL). Purge and fill the reaction vessel with nitrogen (3×), then with hydrogen (3×, 55 psi). Seal the reaction vessel at about 55 psi, and stir the mixture at room temperature overnight. Filter the reaction mixture through a Celite® pad, and wash the filter cake with methanol. Concentrate under reduced pressure and purify the crude residue by flash chromatography (2.5% methanol/methylene chloride) to give the title compound. LCMS (Method D): m/z 387.1 (M+1, APCI); 1H NMR (DMSO-d6): δ 7.97 (d, 1H), 7.88 (d, 1H), 7.57 (d, 1H), 7.42 (dd, 1H), 6.94 (t, 1H), 6.24 (d, 1H), 6.20 (m, 1H), 5.26 (s, 2H), 5.07 (s, 2H), 4.03-4.06 (m, 1H), 3.01 (dd, 1H), 2.72-2.86 (m, 2H), 2.55 (dd, 1H), 2.38-2.46 (m, 1H), 1.98-2.02 (m, 2H), 1.79-1.87 (m, 1H), 1.04 (d, 3H), 1.02 (d, 3H).

Provenance & Evidence