Water → 4-bromo-6-methyl-1H,6H,7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056954Notes

Reaction equation

HRID 1056954 reaction equation
[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][N:10](S(C3C=CC(C)=CC=3)(=O)=O)[C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[OH-].[Na+].O>C(O)C>[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][NH:10][C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 896563044-Bromo-1,6-dihydro-6-methyl-1-((4-methylphenyl)sulfonyl)-7H-pyrrolo(2,3-c)pyridin-7-one

Product 1

HCID 573297664-bromo-6-methyl-1H,6H,7H-pyrrolo[2,3-c]pyridin-7-oneYield 108.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 4-bromo-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (5.81 g, 15.2 mmol) in ethanol (100 mL) was treated with 3.0 M sodium hydroxide in water (50.8 mL, 152 mmol) and stirred at 20° C. for 16 h. The reaction mixture was concentrated in vacuo to remove most of the ethanol. The remaining aqueous layer was neutralized with concentrated HCl to pH ˜7 and extracted with ethyl acetate (2×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated to give the desired product (3.74 g, quantitative) which was used without further purification. LCMS calculated for C8H8BrN2O (M+H)+: m/z=227.0, 229.0. found: 227.0, 228.9.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove most of the ethanol
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6681ac83dd14478d98fc7a54cf5cd8d9
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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