Ethyl bromoacetate → HCID 69483666, compound

Participants

Reaction Steps

To a stirred solution of (±)-6-cyano-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid methyl-phenyl-amide (0.14 g, 0.43 mmol) in dry DMF (1.5 ml) is added KOtBu (58 mg, 0.52 mmol) and ethyl bromoacetate (79 mg, 0.47 mmol). The reaction mixture is stirred at rt overnight, then poured into saturated aqueous KH2PO4 and extracted with CH2Cl2. The combined organic layers are washed with H2O and brine, dried over Na2SO4, filtered and evaporated. The residue is purified by column chromatography on silica gel (hexane/EtOAc 1:1) to provide subtitle compound (91 mg) as a beige solid in 51% yield. tR (LC-3) 1.15 min; ESI-MS (positive ion): m/z 416.09 [M+H]+ (calcd 415.19 for C25H25N3O3). 1H-NMR (CDCl3): 1.13 (t, J=7.0 Hz, 3H); 1.79 (m, 1H); 2.05 (m, 1H); 2.25 (m, 1H); 2.65 (m, 1H); 2.72 (m, 2H); 3.19 (s, 3H); 3.24 (m, 1H); 4.07 (q, J=7.0 Hz, 2H); 5.00 (d, J=3.3 Hz, 2H); 7.33 (m, 1H); 7.41 (m, 5H); 7.50 (d, J=8.0 Hz, 1H); 7.87 (s, 1H).

Provenance & Evidence