Sodium Chloride → 5-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 500723Notes

Reaction equation

HRID 500723 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[Li+].[CH3:23]C([N-]C(C)C)C.CI.[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:23])[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 578562815-bromo-1-(4-bromophenylsulfonyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 684585315-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-bromo-1-(4-bromophenylsulfonyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine (B-6-2) (0.9 g, 2.56 mmol) in THF (20 mL) was added dropwise LDA (15 mL, 0.2 M in THF) at −40° C. The mixture was stirred at −10˜−20° C. for 0.5 hour. Methyl iodide (0.55 g 3.84 mmol) was added dropwise at −40˜−30° C. The reaction was stirred at room temperature overnight. LC-MS showed that the reaction was complete. Saturated aqueous NaCl (10 mL) and EtOAc (10 mL) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated to give 5-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-3) (0.9 g, 96.3%, containing some starting material (B-6-2) as a light yellow solid.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-329d362b603e47c5b75343c6d44dffdc
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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