Reaction #487565

Reaction equation

NaOH

1H-pyrrolo[2,3-b]pyridine 7-oxide

N,N-dimethylformamide

methanesulfonyl chloride

→

wet pale orange solid

Yield 135.4%

4-Chloro-1H-pyrrolo[2,3-b]pyridine

Yield 135.4%

Solvents

water

Conditions

Workup

1. 1
   Temperaturecooled to 40° C
2. 2
   Temperaturethe resulting suspension was cooled to 0° C
3. 3
   FiltrationThe mixture was filtered
4. 4
   Washwashed with water (×3)

Procedure

To a 50° C. pink solution of 1H-pyrrolo[2,3-b]pyridine 7-oxide (2.47 g, 0.0184 mol) in N,N-dimethylformamide (13.3 mL, 0.172 mol) was added methanesulfonyl chloride (4.0 mL, 0.052 mol). The pink color changed to orange. The mixture was heated to 73° C. for 2 h, and cooled to 40° C. Then 35 mL of water was added and the resulting suspension was cooled to 0° C. NaOH was added to adjust the pH of the mixture to ˜7. The mixture was filtered and washed with water (×3) to give 3.8 g of wet pale orange solid that was dried at 40° C. overnight to give 2.35 g (82.2% yield).

Source