Water → HCID 11543477, compound

HRID 1867573Notes

Reaction equation

HRID 1867573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([F:13])[F:12].[H-].[Na+].Br[CH2:17][C:18]([NH2:20])=[O:19].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:17][C:18]([NH2:20])=[O:19])[C:6](=[O:11])[C:5]2([F:13])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 53491513HCID 53491513, compound

Product 1

HCID 11543477HCID 11543477, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-chloro-3,3-difluoro-1,3-dihydro-2H-indol-2-one 4 (2.55 g, 12.5 mmol) is dissolved in dry DMF (20 ml) under a nitrogen atmosphere. The solution is cooled at 0° C. and NaH (0.547 g, 13.8 mmol, 60% dispersion) is carefully added portionwise. When the nitrogen evolution ceases, bromoacetamide (2.05 g, 15.0 mmol) is added. After 30 minutes, the mixture is poured into cold water and the solid is filtered off and washed with water. The crude material is directly recrystallized in acetone/water affording of 2-(5-chloro-3,3-difluoro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 12 as a pink solid.

Workup

  1. filtrationthe solid is filtered off
  2. washwashed with water
  3. customThe crude material is directly recrystallized in acetone/water

Sources & evidence

ORD record
ord-93485ffa0b45467dbb63a7994fbfc8cd
Source dataset
uspto-grants-2009_12
Patent number
US07632856B2

Reaction notes

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