Potassium trimethylsilanolate → 13-cyclohexyl-3-methoxy-6-(1,3-oxazol-2-yl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

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Reaction Steps

Methyl 13-cyclohexyl-3-methoxy-6-(1,3-oxazol-2-yl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (75.4 mg, 0.16 mMol) was dissolved in 2 mL of THF and potassium trimethylsilanolate (103 mg, 0.80 mMol) added to the reaction. The reaction was stirred at room temperature under a nitrogen atmosphere for 19 hrs. The reaction was partitioned between ethyl acetate and 1N aqueous hydrochloric acid. The organic phase was washed sequentially with 1N aqueous hydrochloric acid and brine, dried over magnesium sulfate and volatiles removed in vacuuo to yield 68 mg (93%) of the title product as a yellow solid. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.18-1.33 (1 H, m), 1.36-1.45 (2 H, m), 1.58 (1 H, br. s.), 1.79 (2 H, d, J=10.07 Hz), 1.96 (1 H, br. s.), 2.08 (3 H, br. s.), 2.88 (1 H, t, J=12.05 Hz), 3.94 (3 H, s), 4.44 (1 H, br. s.), 6.00 (1 H, br. s.), 7.04 (1 H, d, J=2.75 Hz), 7.09 (1 H, dd, J=8.70, 2.59 Hz), 7.31 (1 H, s), 7.56 (1 H, d, J=8.85 Hz), 7.65 (1 H, s), 7.68 (1 H, s), 7.82 (1 H, dd, J=8.55, 1.22 Hz), 7.90 (1 H, d, J=8.55 Hz), 8.54 (1 H, s). HPLC analysis: Shimadzu Analytical HPLC using Discovery VP software: % A=10% methanol, 90% water, 0.1% trifluoroacetic acid; % B=90% methanol, 10% water, 0.1% trifluoroacetic acid; Initial % B=50; Final % B=100; Gradient=5 min; Runtime=6 min; Flow rate=5 ml/min; Wavelength=220 nm; Column=Phenomenex Luna 3.0 mm×50 mm S10. Retention Time=3.83 min, purity 96%. Flow injection Mass Spectrometry: MS m/z 455(MH+), m/z 453(M-H)−.

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