Reaction #162215

Reaction equation

NaH

5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-ol

toluenesulfonyl chloride

DMF

→

desired product

5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ol

Conditions

Workup

1. 1
   ConcentrationThe mixture was then concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe crude oil was dissolved in 100 mL EtOAc
3. 3
   Washwashed with water (2×50 mL) and brine
4. 4
   DryingThe organic phase was dried over sodium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe resulting residue was purified via silica gel chromatography (10% EtOAc/Hexanes)

Procedure

To a solution of 5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-ol (1.2 g, 7.9 mmol) in 80 mL DMF at 0° C. was added toluenesulfonyl chloride (1.8 g, 9.5 mmol) followed by NaH (0.8 g, 19.7 mmol, 60% w/w). The reaction was slowly warmed to 45° C. after 3 hours and stirred for an additional 3 hours. The mixture was then concentrated in vacuo. The crude oil was dissolved in 100 mL EtOAc and washed with water (2×50 mL) and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (10% EtOAc/Hexanes) to afford 1.5 g of the desired product.

Source