1,4-Dioxane → HCID 58382334, compound

Participants

Reaction Steps

5-Allyl-4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (3.90 g, 11.2 mmol) in 1,4-dioxane (75 mL) and water (15 mL) was treated with NaIO4 (9.62 g, 45.0 mmol) and OsO4 (2.5% in t-BuOH, 5.65 mL, 0.450 mmol). The mixture was stirred at rt for about 1 h then diluted with EtOAc (100 mL). The solids were collected by filtration and the cake was washed with EtOAc (2×100 mL). The filtrate was washed with water (100 mL) and saturated aqueous NaCl (50 mL) then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel to give 2-(4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetaldehyde as a mixture of aldehyde and hydrate (1.45 g, 37%); LC/MS (Table 2, Method b) Rt=2.51 min; MS m/z 349 (M+H)+.

Provenance & Evidence