Methyl iodide → 2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1049384Notes

Reaction equation

HRID 1049384 reaction equation
[CH:1](NC(C)C)(C)C.[Li].[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][N:25]=3)[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.IC>C1COCC1.CCCCCCC.C1COCC1.O>[CH3:1][C:19]1[N:18]([S:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:17])=[O:16])[C:26]2[C:21]([CH:20]=1)=[CH:22][CH:23]=[CH:24][N:25]=2

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 45051747Lithium diisopropylamine

Product 1

HCID 12363722-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 21263495Tetrahydrofuran heptaneSolvent

Procedure

4.8 ml of a 2M solution of lithium diisopropylamine in THF/heptane are added dropwise over the course of 60 min. to a solution of 1 g of 1-(benzenesulfonyl)-7-azaindole in 20 ml of THF at −70° C. under an N2 atmosphere. The mixture is allowed to warm to 20° over the course of 50 minutes. The suspension is cooled to −70°, and a solution of 1.1, g of iodomethane in 20 ml of THF is added dropwise over the course of 20 minutes. The mixture is stirred at −70° for one hour and subsequently at room temperature for 14 h. The mixture is diluted with water and extracted with dichloromethane. The extract is dried over sodium sulfate, filtered, the solvent is removed and crystallised from cyclohexane, giving 0.68 g of 2-methyl-1-(benzenesulfonyl)-7-azaindole, M˜272.32 g/mol, M+H found 273, NMR corresponds.

Workup

  1. temperatureto warm to 20° over the course of 50 minutes
  2. temperatureThe suspension is cooled to −70°
  3. additionis added dropwise over the course of 20 minutes
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed
  8. customcrystallised from cyclohexane

Sources & evidence

ORD record
ord-7674cead4a364b9fbedf4e8e317ed304
Source dataset
uspto-grants-2016_07
Patent number
US09382244B2

Reaction notes

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