m-Chloroperbenzoic acid → 5-Fluoro-3-[5-fluoro-4-(methylsulfinyl)-2-pyrimidinyl]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

5-fluoro-3-[5-fluoro-4-(methylthio)pyrimidin-2-yl]-1-tosyl-1H-pyrrolo[2,3-b]pyridine, 44b, (48.2 g, 111.5 mmol) was dissolved in dichloromethane (2.3 L) and treated portionwise with m-CPBA (27.5 g, 122.6 mmol) while keeping the temperature below 20° C. After addition was complete, the reaction was stirred at room temperature for 2 hours, then treated with another portion of m-CPBA (1.9 g) and stirred for another hour. The reaction mixture was washed with 12% aqueous K2CO3 (2×1.0 L) and the organic layer was dried on Na2SO4 and concentrated in vacuo to provide 50 g of 5-fluoro-3-[5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl]-1-tosyl-1H-pyrrolo[2,3-b]pyridine as a yellow solid.

Provenance & Evidence