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

HRID 1397835Notes

Reaction equation

HRID 1397835 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>ClCCl>[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), 150 mL of dichloromethane was added under an atmosphere of nitrogen with the temperature maintained below 5° C. To this, 5-bromo-1H-pyrrolo[2,3-b]pyridine (8, 1.64 g, 8.34 mmol) in 20 mL of dichloromethane was added. The reaction was stirred for 60 minutes and 2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride (7, 3.50 g, 11.8 mmol) in 20 mL of dichloromethane was added. The reaction was stirred for 6 hours, then 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, filtered and the filtrate concentrated under vacuum. The desired compound was isolated by silica gel column chromatography (dichloromethane/methanol 5%) to give a white solid (9, 1.2 g, 31.4%). MS(ESI) [M+H+]+=460.0, 462.0.

Workup

  1. temperaturemaintained below 5° C
  2. stirringThe reaction was stirred for 6 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-ffd1923f78c7476d9c3bbc1ac83c7b96
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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