Sodium hydride → 1H-Pyrrolo[2,3-B]pyridine-1-sulfonamide, N,N-dimethyl-3-(2,2,2-trifluoroacetyl)-

HRID 244397Notes

Reaction equation

HRID 244397 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[H-].[Na+].[CH3:18][N:19]([CH3:24])[S:20](Cl)(=[O:22])=[O:21]>CN(C=O)C.C(=O)(O)[O-].[Na+]>[CH3:18][N:19]([CH3:24])[S:20]([N:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[C:5]([C:3](=[O:4])[C:2]([F:1])([F:14])[F:15])=[CH:6]1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 57078082,2,2-trifluoro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

Product 1

HCID 497590101H-Pyrrolo[2,3-B]pyridine-1-sulfonamide, N,N-dimethyl-3-(2,2,2-trifluoroacetyl)-Yield 54.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 107 mg (0.5 mmol) of 2,2,2-trifluoro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone in 2 mL of DMF was added 60% sodium hydride in mineral oil followed by 80 mg (0.56 mmol) of N,N-dimethylsulfamoyl chloride. The mixture stirred for 30 minutes and was then diluted with 10 mL of saturated aqueous sodium bicarbonate and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 7 mL portions of brine, three 7 mL portions of saturated aqueous ammonium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was adsorbed onto silica gel and chromatographed on silica gel eluting with ethyl acetate-hexanes (10-100% gradient) to afford 88 mg (54%) of 3-(2,2,2-trifluoroacetyl)pyrrolo[2,3-b]pyridine-1-sulfonic acid dimethylamide as a white solid.

Workup

  1. extractionextracted with three 7 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with three 7 mL portions of brine, three 7 mL portions of saturated aqueous ammonium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel eluting with ethyl acetate-hexanes (10-100% gradient)

Sources & evidence

ORD record
ord-eac70047e679466591c4f02a832d1085
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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