1,1'-Carbonyldiimidazole → HCID 69058821, compound

Participants

Reaction Steps

To a solution of indole-2-carboxylic acid (388 mg, 2.40 mmol) and methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (401 mg, 2.00 mmol) in THF (16 mL) was added CDI (356 mg, 2.20 mmol). After 18 h at rt, the mixture was concentrated, diluted with CH2Cl2, washed with satd. aq. Na2CO3 and water, dried (Na2SO4), and concentrated. The residue was purified by FCC to give the title compound (565 mg, 69%). MS (ESI): mass calcd. for C19H25N3O3, 343.19; m/z found, 344 [M+H]+. 1H NMR (CDCl3): 9.73 (s, 1H), 7.67 (d, J=8.0, 1H), 7.46 (dd, J=8.3, 0.8, 1H), 7.29 (t, J=8.2, 1H), 6.89 (d, J=1.3, 1H), 4.89 (br s, 1H), 4.26-3.49 (m, 4H), 2.85 (s, 3H), 2.36-1.96 (m, 2H), 1.76 (s, 1H), 1.49 (s, 9H). Anal. Calcd for C19H25N3O3: C, 66.45; H, 7.34; N, 12.24. Found: C, 66.42; H, 7.55; N, 12.10.

Provenance & Evidence