HCID 25174433, compound → HCID 25174434, compound

Participants

Reaction Steps

A mixture of (R)—N-(6-cyano-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-5-nitro-1H-indole-2-carboxamide (200 mg, 0.534 mmol) (prepared as described in Example 8) and 10% Pd/C (80 mg) in 1:1 THF/MeOH (24 mL) was stirred at rt under H2, provided a H2 balloon, for 3 hr. The catalyst was removed by suction filtration, and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (50 mL), washed with brine (20 mL), and dried over anhydrous MgSO4. It was concentrated under vacuum, and the residue was applied to ISCO (12 g silica gel, 40-55% ethyl acetate/hexane) to afford the desired title product (106 mg, 58% yield) as a pale yellow solid. LCMS (M+H)=345.38. 1H NMR (500 MHz, DMSO-d6) δ: 11.1 (s, 1H), 8.33 (d, J=9.3 Hz, 1H), 7.69 (d, J=8.2 Hz, 1H), 7.59 (s, 1H), 7.45 (d, J=7.7 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 6.98 (s, 1H), 6.68 (s, 1H), 6.61 (d, J=8.8 Hz, 1H), 5.35 (d, J=9.3 Hz), 4.60 (br. s, 2H), 2.86 (dd, J=23.6, 16.5 Hz, 2H), 1.20 (s, 3H), 0.93 (s, 3H).

Provenance & Evidence