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

HRID 527075Notes

Reaction equation

HRID 527075 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-4bbca466b59c460d99c85447338030e1
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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