Methyl iodide → 4-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

HRID 244640Notes

Reaction equation

HRID 244640 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:11]=12.CI>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:17]([CH3:1])=[CH:18][C:11]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 497590984-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

1.8M Lithium diisopropylamide (270 ml) was added dropwise over 20 min to a solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (82 g) in dry THF (820 ml) and the reaction was stirred at −45° C. for 30 min. Methyl iodide (90 ml) was added drop wise to the solution and the mixture was stirred at −45° C. for 45 min, then allowed to warm to RT. The reaction was quenched with water. The organic layer was collected and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was triturated with ethyl acetate:cyclohexane (3:1). The solid material was collected and washed with ethyl acetate:cyclohexane (3:1) and dried in vacuo at 35° C. This residue was dissolved in DCM, washed with water, dried over magnesium sulphate and the solvent removed in vacuo to give the title compound (37.6 g) as a cream solid.

Workup

  1. stirringthe mixture was stirred at −45° C. for 45 min
  2. temperatureto warm to RT
  3. customThe reaction was quenched with water
  4. customThe organic layer was collected
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ethyl acetate:cyclohexane (3:1)
  10. customThe solid material was collected
  11. washwashed with ethyl acetate:cyclohexane (3:1)
  12. customdried in vacuo at 35° C
  13. dissolutionThis residue was dissolved in DCM
  14. washwashed with water
  15. dry with materialdried over magnesium sulphate
  16. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4d8301648d1d4749a7ebd2291661b2b2
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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