1-(Phenylsulfonyl)-4-azaindole synthesis

Yield:677302-44-2 94%

Reaction Conditions:

Stage #1: pyrrolo<3,2-b>pyridinewith sodium hydride in tetrahydrofuran;
Stage #2: benzenesulfonyl chloride in tetrahydrofuran at 20;

Steps:

108

Preparation 108: l-(Benzenesulfonyl)pyrrolo[3,2-b]pyridine; [1033] Sodium hydride (0.74g, 16.9mmol) was dissolved in 3OmL of anhydrous tetrahy- drofuran. lH-pyrrolo[3,2-b]pyridine (Ig, 8.46mmol) dissolved in 1OmL of anhydrous tetrahydrofuran was slowly added in drops, and the mixture was stirred for 30 min. Benzenesulfonyl chloride (3g, 16.9mmol) dissolved in 1OmL of anhydrous tetrahydrofuran was slowly added in drops, and the mixture was stirred for 15 h at room temperature. The reaction solution was poured to 0.1 N hydrochloric acid, which was then controlled to basic using aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was collected, and distilled under reduced pressure. The remaining substance was purified by column chromatography to give 2.06g (8mmol, Yield 94%) of the title compound.[1034] NMR ¹H-NMR(CDCl₃) δ 8.54(1H, d), 8.27(1H, d), 7.87(2H, d), 7.80(1H, d), 7.57(1H, t), 7.47(2H, t), 7.24(1H, dd), 6.88(1H, d)[1035] Mass(EI): 259(M⁺+1)

References:

WO2010/93191,2010,A2 Location in patent:Paragraph 1031-1035