Methyl iodide → 5-fluoro-4-methoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 75034Notes

Reaction equation

HRID 75034 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[OH:21].CI.[C:24]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[F:1][C:2]1[C:3]([O:21][CH3:24])=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178427346HCID 178427346, compound2×

Product 1

HCID 680078835-fluoro-4-methoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ol, 68a, (0.70 g, 2.29 mmol) in DMF (25 mL) was added methyliodide (0.14 mL, 2.29 mmol) and K2CO3 (0.32 g, 2.29 mmol). The reaction mixture was stirred for 3 hours at ambient temperature. The reaction was diluted with deionized water and EtOAc. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 720 mg of the desired product that was used in next step without further purification.

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa5cbf5cb993445f972e48bbc6b7a88a
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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