1,3-Dimethoxy-2-propanol → HCID 66897808, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 7-hydroxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (2.75 g), tributylphosphine (3.7 mL), 1,1′-(azodicarbonyl)dipiperidine (3.8 g), 1,3-dimethoxypropan-2-ol (1.8 g) and tetrahydrofuran (50 mL) was stirred at 50° C. for 8 h. Tributylphosphine (1.9 mL), 1,1′-(azodicarbonyl)dipiperidine (1.9 g) and 1,3-dimethoxypropan-2-ol (0.9 g) were added to the mixture again, and the mixture was stirred at 50° C. for 8 h. Furthermore, tributylphosphine (3.7 mL), 1,1′-(azodicarbonyl)dipiperidine (3.8 g) and 1,3-dimethoxypropan-2-ol (1.8 g) were added to the mixture. After stirring at 50° C. for 24 h, the mixture was cooled to 0° C. and a precipitate was removed by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 80/20, volume ratio) twice, followed by basic silica gel column chromatography (ethyl acetate/hexane 20/80 to 85/15) to give the crude title compound (3.42 g) as a yellow oil. MS 465 (MH+).

Provenance & Evidence