Water → HCID 21931732, compound

HRID 2209283Notes

Reaction equation

HRID 2209283 reaction equation
[Cl:1][C:2]1[N:7]=C2N[C:9](=O)[CH2:10][C:5]2=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:15].O.[CH3:17][N:18]([CH:20]=[O:21])[CH3:19]>[Cl-].[Na+].O.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:17]2[N:18]([CH3:19])[C:20](=[O:21])[C:10]([CH3:9])([CH3:15])[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 219070476-Chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 21931732HCID 21931732, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 6-chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (50 mg, 0.30 mmol) in DMF (1 mL) at 0° C. was added NaH (48 mg, 1.2 mmol, 60%), and the reaction was stirred for 5 minutes. Iodomethane (210 mg, 1.5 mmol) was added and the reaction became a thick slurry. DMF (0.5 mL) was added and the reaction was stirred at room temperature for 90 minutes. Water, EtOAc, and brine were added, the layers were separated and the organic layer was washed with brine. The organics were dried over MgSO4, filtered and concentrated to afford 6-chloro-1,3,3-trimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 7.28 which was used without further purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C10H12ClN2O: 211.1; found: 211.0.

Workup

  1. stirringthe reaction was stirred at room temperature for 90 minutes
  2. customthe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c88d4d85d3904d1086c79f9e11e9607f
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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