Hydrochloric Acid → methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylate

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Reaction Steps

To a stirred solution of dimethyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (2.6 g, 6.1 mmol) in DMF (60 mL) was added LiOH (1.45 g, 60 mmol) and the reaction mixture was heated at 60° C. for 2d. The reaction mixture was cooled internally with ice, acidified with 1M aqueous HCl (pH<2) and extracted with EtOAc (350 mL). The organics were washed with H2O (˜150 mL), brine (˜150 mL), dried (MgSO4), filtered and concentrated. The solids were triturated with Et2O/hexanes (1:2) and collected to yield methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylate, 6-carboxylic acid (2.06 g, 4.96 mmol. 81%) as a fluffy yellow solid. 1HNMR (500 MHz, DMSO-d6) δ 8.18 (s, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.88 (s, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.67–7.55 (m, 4H), 5.58 (br s, 1H), 4.15 (br s, 1H), 3.90 (s, 3H), 2.84–2.75 (m, 1H), 2.10–1.65 (m, 6H), 1.49–1.07 (m, 4H). LCMS: m/e 416 (M+H)+, ret time 1.47 min, column A, 2 minute gradient.

Provenance & Evidence