Hydrochloric Acid → HCID 22477256, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamine {prepared by treating a solution of diisopropylamine (33.6 mL) in tetrahydrofuran (250 mL) with butyl lithium in hexanes (70.4 mL, 2.5M) at −35° C., at −75° C., was treated dropwise with a solution of 1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [40 g, Reference Example 9(a)] in dry tetrahydrofuran (250 mL) at −75° C. whilst maintaining the reaction temperature below −60° C. After stirring at −75° C. for 3 hours the reaction mixture was allowed to warm to 5° C. over 2 hours then recooled to −75° C. and then treated with dimethylformamide (62 mL). The reaction mixture was left to warm to room temperature over 1 hour then poured into hydrochloric acid (800 mL, 1%) and then evaporated to remove the tetrahydrofuran. The resulting suspension was filtered and the solid was washed with water, then dried and then was subjected to flash column chromatography on silica eluting with dichloromethane to give the title compound (24.37 g) as a white solid.

Provenance & Evidence