Sodium Hydroxide → HCID 67147812, compound

Participants

Reaction Steps

1 cm3 of a 1M solution of tetrabutylammonium fluoride (TBAF) in tetrahydrofuran is added, at a temperature in the region of 20° C., to a solution of 0.14 g of cyclohexyl [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine in 10 cm3 of tetrahydrofuran. The reaction medium is stirred at this same temperature for 15 hours, and then refluxed for 24 hours. After cooling, the reaction medium is evaporated to dryness under reduced pressure. 4 cm3 of water are added. The solid formed is filtered off on a sinter funnel, and washed with water and then with ethyl ether. The solid obtained is taken up in water and the medium is basified to pH 10 with 0.1N sodium hydroxide. The product is extracted five times with dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.029 g of cyclohexyl [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine is thus obtained, the characteristics of which are as follows:

Provenance & Evidence