Water → 1-Propanesulfonamide, N-[3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-

HRID 217607Notes

Reaction equation

HRID 217607 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1.[F:15][C:16]1[C:24]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])=[CH:23][CH:22]=[C:21]([F:32])[C:17]=1[C:18](Cl)=[O:19].O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]2[C:14]([C:18]([C:17]3[C:16]([F:15])=[C:24]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=3[F:32])=[O:19])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 580868612,6-Difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride

Product 1

HCID 119845561-Propanesulfonamide, N-[3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To aluminum trichloride (8.89 g, 66.7 mmol) was added methylene chloride (150 mL) under an atmosphere of nitrogen below 5° C. Into this, 5-bromo-1H-pyrrolo[2,3-b]pyridine (55, 1.64 g, 8.34 mmol) in methylene chloride (20 mL) was added. The reaction was stirred for 60.0 minutes and 2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride (54, 3.50 g, 11.8 mmol) in methylene chloride (20 mL) was added. The reaction was stirred for 6 hours and warmed to room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtrated and concentrated. The desired compound was isolated by silica gel column chromatography (methylene chloride/methanol 5%) to give a white solid (56, 1.2 g, 31.4%). MS (ESI) [M+H+]+=460.0, 462.0.

Workup

  1. stirringThe reaction was stirred for 6 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-53145a70d33541a3918f8bb911555e46
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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