Ethanolamine → 1-(chloromethyl)-N-(2-hydroxyethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

Participants

Reaction Conditions

Reaction Steps

(Scheme C). A solution of 116 (456 mg, 1.00 mmol) in TV (5 mL) and CH2Cl2 (5 mL) was treated at 0° C. with a solution of ethanolamine (134 mg, 2.19 mmol) in THF (0.5 mL). The mixture was stirred at 0° C. for 5 min, then warmed to room temperature for 10 min and treated with a solution of Cs2CO3 (980 mg, 3 mmol) in MeOH (20 mL). After stirring at room temperature for a further 10 min, the mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with water (×2), dried, filtered through a short column of silica gel, and then concentrated to a small volume and diluted with i-Pr2O/hexane to give 1-(chloromethyl)-N-(2-hydroxyethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide (121) (346 mg, 90%): mp 173-174° C.; 1H NMR [(CD3)2SO] δ 8.57 (d, J=1.6 Hz, 1H), 8.03 (d, J=8.9 Hz, 1H), 7.80 (dd, J=8.9, 1.7 Hz, 1H), 7.77 (s, 1H), 7.69 (br s, 1H), 6.73 (s, 1H), 4.64 (t, J=5.6 Hz, 1H), 4.29-4.19 (m, 1H), 3.95-3.84 (m, 2H), 3.80 (dd, J=11.0, 8.4 Hz, 1H), 3.74 (dd, J=10.4, 3.3 Hz, 1H), 3.35 (after D2O exchange, t, J=6.3 Hz, 2H), 2.81 (t, J=6.3 Hz, 2H). Anal. (C15H16C11N3O5S) C, H, N.

Provenance & Evidence