1-Methoxy-2-propanol → HCID 66897975, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-[2-(benzylsulfanyl)-3,3-dimethoxypropyl]-7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (1.73 g), tributylphosphine (1.4 mL) and 1-methoxypropan-2-ol (0.59 mL) in tetrahydrofuran (50 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.53 g) at room temperature under argon atmosphere. The whole mixture was stirred at 50° C. for 4 h, and tributylphosphine (1.4 mL), and 1-methoxypropan-2-ol (0.59 mL) and 1,1′-(azodicarbonyl)dipiperidine (1.53 g) were added thereto. After stirred at 50° C. for 3 h, the reaction mixture was concentrated in vacuo. The residue was diluted with diethyl ether and the insoluble materials were removed by filtration and washed with diethyl ether. The combined filtrate and washings were concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate:hexane=35:65 to 60:40) to give a light yellow oil. The oil was partitioned between ethyl acetate and water. The organic layer was washed with successively water and brine, dried (MgSO4), filtered, and concentrated to give a yellow oil, which was purified by silica gel chromatography (ethyl acetate:hexane=35:65 to 70:30, volume ratio) to give the title compound (1.6 g, 82%) as a pale yellow oil. MS 641 (MH+).

Provenance & Evidence