N,N-Dimethylaniline → 8-Chloro-5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b; 4',3'-d]pyrrole

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Reaction Steps

Compound 31 (50 mg, 0.136 mmol) stirred in POCl3 (2 mL) with dimethylaniline (0.1 mL) at 108° C. under nitrogen for 16 h. The solution was concentrated and dissolved in CH2Cl2. Ice and saturated NaHCO3 solution were added, and organics were extracted (2×) with CH2Cl2, dried (MgSO4), and concentrated in vacuo. Purification by silica gel chromatography (3% MeOH/CH2Cl2) gave 36 mg (69%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, MeOD-d4/CDCl3): δ 8.46 (s, 1H), 8.22 (s, 1H), 8.14 (s, 1H), 8.11 (d, 1H, J=8.0 Hz), 8.01 (d, 1H, J=8.0 Hz), 7.89 (t, 1H, J=8.0 Hz), 7.84 (s, 1H), 7.76 (s, 1H), 3.28 (q, 2H, J=7.2 Hz), 2.38 (s, 3H), 1.31 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C19H16ClN3O2S, 386, 388; found 386, 388.

Provenance & Evidence