5-Benzyloxyindole → HCID 59603424, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-benzyloxyindole (0.245 g) in DMF (5 mL) was cooled to 0° C. then sodium hydride (0.06 g) added. After 30 min [1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-dimethyl-amine (0.395 g) was added. The reaction vessel was sealed and heated at 150° C. After 1 h the reaction mixture was cooled to room temperature and diluted with water and saturated aqueous sodium chloride solution. The solid separated was filtered and then purified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane). The residue obtained was dissolved in ethanol (30 mL) and dichloromethane (20 mL). Palladium on carbon (10%, 40 mg) was added. The mixture was degassed and was purged with hydrogen, and continued under a hydrogen balloon overnight. The reaction mixture was filtered through solka floc. The filtrate was concentrated and purified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane) to furnish 132 (0.012 g, 15%) as a white solid. MS m/e 493 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.7-1.8 (m, 2H), 2.0-2.1 (d, 2H), 2.3 (m, 3H), 2.7 (s, 6H), 2.95 (d, 2H), 3.2 (m, 2H), 3.89-4.04 (m, 10H), 6.5 (d, 1H), 6.75 (d, 1H), 6.95 (d, 1H), 7.2 (br. s, 1H), 7.4 (s, 1H), 8.2 (d, 1H), 8.5 (d, 1H).

Provenance & Evidence