Water → Propane-1-sulfonic acid{3-[5-(4-chloro-phenyl)1-(2,6-dichloro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-methyl-amide

HRID 1507464Notes

Reaction equation

HRID 1507464 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][N:14]([C:34](=[O:43])[C:35]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=4[Cl:42])[C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:44]I.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([N:26]([CH3:44])[S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][N:14]([C:34](=[O:43])[C:35]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=4[Cl:42])[C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 51001026N-(3-(5-(4-chlorophenyl)-1-(2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide

Product 1

HCID 118194079Propane-1-sulfonic acid{3-[5-(4-chloro-phenyl)1-(2,6-dichloro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-methyl-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propane-1-sulfonic acid{3-[5-(4-chloro-phenyl)-1-(2,6-dichloro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide (0.5 g, 0.8 mmol) were dissolved in 1 ml dimethylformamide 0.1 g sodium carbonate was added under stirring at room temperature. Methyl iodide (70 μl, 0.16 g, 1.1 mmol) was added dropwise under vigorous stirring at room temperature by a syringe. The reaction mixture was stirred at room temperature overnight. Water was added to the stirred suspension, and the mixture was stirred for 1 hour. The reaction mixture was extracted with ethyl acetate twice (2×20 ml). The organic layer was dried over sodium sulfate. After drying of the organic layer, the solvent was evaporated under reduced pressure at 46° C. The brownish remaining crude product was used for the further synthesis without purification.

Workup

  1. additionwas added
  2. stirringunder vigorous stirring at room temperature by a syringe
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. stirringthe mixture was stirred for 1 hour
  5. extractionThe reaction mixture was extracted with ethyl acetate twice (2×20 ml)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customAfter drying of the organic layer
  8. customthe solvent was evaporated under reduced pressure at 46° C
  9. customwas used for the further synthesis without purification

Sources & evidence

ORD record
ord-893c23731a304c71af8fb9fd3c9b4948
Source dataset
uspto-grants-2015_12
Patent number
US09221815B2

Reaction notes

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