Dichloromethane → HCID 68465366, compound

Participants

Reaction Steps

To a stirred solution methyl(triphenylphosphoranylidene)acetate (2.39 g, 0.0071 moles) in dry DCM (20 mL) was added tert-butyl 2-[5-(formyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (1.35 g, 0.0036 moles) at 0° C. in dry DCM (10 mL). After stirring for >12 hours, the reaction mixture was washed with 10% NaHCO3 solution (20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The compound was purified through silica gel column chromatography using 15% EtOAc in hexane to give tert-butyl 2-{5-[(1E)-3-methoxy-3-oxoprop-1-enyl]pyrimidin-2-yl}-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (1.22 g, 78% yield). 1H NMR (DMSO-d6, 400 MHz) ppm: 8.81 (s, 2H, 2Ar—H), 8.06 (d, 1H, J=8 Hz, 1Ar—H), 7.54 (d, 1H, J=16 Hz, ═CH), 7.50 (d, 1H, J=8 Hz, 1Ar—H), 7.32-7.23 (m, 2H, 2Ar—H), 6.60 (d, 1H, J=16 Hz, —CH), 5.23 (s, 2H, CH2), 4.19 (t, 2H, CH2), 3.7 (s, 3H, OMe), 2.78 (brs, 2H, CH2), 1.68 (s, 9H, 3CH3). M/e=435 (M+1) (M, 434.488 Calcd. for C24H26N4O4).

Provenance & Evidence