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

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Reaction Steps

Conc. aqueous NH3 (0, 32 mL, 4.7 mmol) was added to a solution of 116 (215 mg, 0.47 mmol) in THF (10 mL) at −78° C. After 10 min water (10 mL), aqueous HCl (2 N, 5 mL, 9.4 mmol), and EtOAc (20 mL) were added and the mixture was allowed to warm to room temperature. Brine was added and the mixture was extracted with EtOAc (×2). The combined extracts were washed with brine and dried, and the EtOAc solution was evaporated onto silica. Chromatography eluting with EtOAc/petroleum ether (1:10 then 1:3 then 2:1) gave 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide (123) (158 mg, 77%) as a pale yellow solid: mp (EtOAc) 274-278° C. (dec.); 1H NMR [(CD3)2SO] δ 9.11 (s, 1H), 8.89 (d, J=1.6 Hz, 1H), 8.50 (d, J=8.9 Hz, 1H), 8.11 (dd, J=8.9, 1.7 Hz, 1H), 7.66 (s, 1H), 4.73-4.64 (m, 2H), 4.57-4.49 (m, 1H), 4.24-4.11 (m, 2H). Anal. (C15H11ClF3N3O5S) C, H, N.

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