HCID 68465366, compound → HCID 68461476, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 2-{5-[(1E)-3-methoxy-3-oxoprop-1-enyl]pyrimidin-2-yl}-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (0.25 g, 0.0005 moles) (See Example 20) in 10 mL of dry THF was added 1:1 mixture of Pd (OH)2 (50 mg) & Pd/C (50 mg) and stirred in the hydrogen atmosphere using balloon. After stirring for >12 hours, the reaction was filtered through a celite pad. The filtrate was concentrated and the crude residue was purified through silica column using 30% EtOAc in hexane to give methyl 3-{2-[9-(tert-butyloxycarbonyl)-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidin-5-yl}propanoate (0.16 g, 63% yield). 1H NMR (DMSO-d6, 400 MHz) ppm: 8.33 (s, 2H, 2Ar—H), 8.06 (d, 1H, J=8 Hz, 1Ar—H), 7.49 (d, 1H, J=8 Hz, 1Ar—H), 7.31-7.22 (m, 2H, 2Ar—H), 5.12 (s, 2H, CH2), 4.09 (t, 2H, J=8 Hz, CH2), 3.57 (s, 3H, OMe), 2.74 (brs, 2H, CH2), 2.7 (t, 2H, CH2), 2.67 (t, 2H, CH2), 1.68 (s, 9H, 3CH3). M/e=437 (M+1) (M, 436.504 Calcd. for C24H28N4O4).

Provenance & Evidence