Methanesulfonyl chloride → HCID 178477812, compound

HRID 1506224Notes

Reaction equation

HRID 1506224 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:11]=[CH:10][NH:9][C:5]2=[N+:6]([O-])[CH:7]=1.CS([Cl:16])(=O)=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:1][C:2]1[C:3]([Cl:16])=[C:4]2[N:11]=[CH:10][NH:9][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178526232HCID 178526232, compound

Product 1

HCID 178477812HCID 178477812, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
73 °C

Procedure

6-Bromo-3H-imidazo[4,5-b]pyridine 4-oxide (1.88 g, 8.82 mmol) in N,N-dimethylformamide (12 mL) was heated to 50° C., mixed with methansulfonyl chloride (8.00 mL, 103 mmol) and stirred at 73° C. for 3 hours. The reaction mixture was cooled with ice and gradually poured into saturated aqueous sodium hydrogen carbonate (75 mL), and the precipitated solid was collected by filtration, washed with water and chloroform and dried under reduced pressure to give the title compound as a dark brown solid (1.07 g, yield 52%).

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water and chloroform
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-99b09c1769904fb2808fc4a13284a878
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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