Tetrahydrofuran → HCID 86627419, compound

Participants

Reaction Conditions

Reaction Steps

7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[3-(4-morpholinylcarbonyl)-2-pyridinyl]-, 1,1-dimethylethyl ester. To a solution of 7H-Indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-(tributylstannyl)-, 1,1-dimethylethyl ester (100 mg, 0.136 mmol) dissolved in THF (2 mL) was added 4-[(2-chloropyridin-3-yl)carbonyl]morpholine (47 mg, 0.21 mmol), TEA (0.029 mL), and tetrakis(triphenylphosphine)palladium (16 mg, 0.014 mmol). This mixture was capped under nitrogen and heated in a microwave at 160° C. for 2 hr. The reaction mixture was filtered purified by prep HPLC under the following conditions: Shimadzu prep. HPLC using Discovery VP software: % A=10% acetonitrile, 90% water, 0.1% TFA; % B=90% acetonitrile, 10% water, 0.1% TFA; Initial % B=30; Final % B=100; Gradient=12 min; Runtime=20 min; Flow rate=40 ml/min; Column=Waters Sunfire 30×100 mm S5. This afforded the title compound (38 mg, 44%) as a yellow paste. MS m/z 634 (MH+).

Provenance & Evidence