1,2-Dichloroethane → HCID 135486190, compound

Participants

Reaction Steps

A solution of 1-(tert-butoxycarbonyl)-2-(1H-indazol-3-yl)-1H-indole-5-carboxylic acid (4-5, 100 mg, 0.265 mmol), N-methyl piperazine (40 μL, 0.32 mmol), EDC (61 mg, 0.32 mmol), and HOAt (43.3 mg, 0.32 mmol)in 5 ml of DMF was treated with triethylamine (90 μL, 0.66 mmol) and mixed for 24 h. The solution was partitioned between ethyl acetate (3×50 mL) and water (75 mL). The combined organics were dried over Na2SO4, filtered and concentrated. The residual oil was dissolved in a 1:1 mixture of dichloromethane/trifluoroacetic acid and mixed for 45 min. The solvent was removed in vacuo and the residue was purified by reverse phase liquid chromatography (H2O/CH3CN gradient with 0.1% 1TFA present) to provide 3-{5-[(4-methylpiperazin-1-yl)carbonyl]-1H-indol-2-yl}-1H-indazole (4-6); 1H NMR (500 MHz, CD3OD) δ 11.36 (s, 1H), 8.14 (d, 1H, J=8.3 Hz), 7.83 (s, 1H), 7.58 (dd, 2H, J=8.5 Hz), 7.45 (t, 1H, J=8.3 Hz), 7.30 (dd, 2H, J=8.06 Hz), 7.17 (s, 1H), 4.55 (bs, 2H), 3.45 (bs, 2H), 3.25 (bs, 2H), 2.98 (s, 3H).

Provenance & Evidence