Ethyl bromoacetate → HCID 22219598, compound

Participants

Reaction Conditions

Reaction Steps

Under N2, a flame-dried, 250-mL, three-necked flask was charged with sodium hydride (0.56 g, 13.9 mmol) and anhydrous DMF (20 mL) and cooled to 0° C. A suspension of tert-butyl 6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate (2.66 g, 9.3 mmol) in anhydrous DMF (30 mL) was added and the mixture was stirred at 0° C. for 1 hour and then at room temperature for 30 m. Ethyl bromoacetate (2.06 mL, 18.6 mmol) was added and the mixture was stirred at room temperature for 16 hours. The mixture was partitioned between EtOAc and water and the organic layer was washed with water and the organic layer concentrated to give 4.32 g of a brown oil. Dissolving the oil in CH2Cl2 and filtration of the resulting precipitate removes unreacted starting material. Column chromatography of the filtrate (elution with 20–50% Et2O/hexane) gave 2.11 g (61%) of the title compound as a white solid: mp 111 –115° C.; 1H NMR (300 MHz, CDCl3) δ 7.37 (d, J=8 Hz, 1 H), 6.93–6.90 (m, 2 H), 6.48 (d, J=3 Hz, 1 H), 4.98 (s, 2 H), 4.24 (q, J=7 Hz, 2 H), 3.60–3.57 (m, 4 H) 3.17–3.13 (m, 2 H), 3.04–3.00 (m, 2 H), 1.44 (s, 9 H), 1.29 (t, J=7 Hz, 3 H); MS (EI), m/z 372 (M+); HRMS (FAB) calcd for C20H26N2O4+H 359.1971. found 359.1972. Anal. Calcd for C21H28N2O4: C, 67.72; H, 7.58; N, 7.52. Found: C, 68.06; H, 7.70; N, 7.73.

Provenance & Evidence