Water → 4-Bromo-1,6-dihydro-6-methyl-1-((4-methylphenyl)sulfonyl)-7H-pyrrolo(2,3-c)pyridin-7-one

HRID 632741

Reaction equation

HRID 632741 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]2[CH:13]=[CH:12][N:11]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:6]=2[C:7](=[O:10])[NH:8][CH:9]=1.I[CH3:25].O>CN(C)C=O>[Br:3][C:4]1[C:5]2[CH:13]=[CH:12][N:11]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:6]=2[C:7](=[O:10])[N:8]([CH3:25])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 896575804-bromo-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Product 1

HCID 896563044-Bromo-1,6-dihydro-6-methyl-1-((4-methylphenyl)sulfonyl)-7H-pyrrolo(2,3-c)pyridin-7-oneYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.875 g, 36.5 mmol, 1.46 g of a 60% in oil dispersion) was added to a stirring solution of 4-bromo-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (11.2 g, 30.4 mmol) in dimethylformamide (217 mL) under nitrogen. After 30 minutes, iodomethane (2.27 mL, 36.5 mmol) was added and the solution was stirred at room temperature for 3 h. Upon addition of water (250 mL) a precipitate formed. The precipitate was collected by vacuum filtration, rinsed with water (50 mL) and dried in a vacuum oven at 55° C. overnight to provide 11.2 g of 4-bromo-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (96%).

Workup

  1. customformed
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washrinsed with water (50 mL)
  4. customdried in a vacuum oven at 55° C. overnight

Sources & evidence

ORD record
ord-0e7a7c5b7f2b4e74a2f216b2c291a745
Source dataset
uspto-grants-2016_04
Patent number
US09321765B2

Linked notes

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