Sodium hydride → HCID 118433961, compound

HRID 1052599Notes

Reaction equation

HRID 1052599 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[H-].[Na+].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:14]([CH3:13])(=[O:16])=[O:15])[CH:9]=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 118433961HCID 118433961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-1H-pyrrolo[2,3-b]pyridine (250 mg, 1.27 mmol) was dissolved in 5 ml N—N, dimethylformamide. Sodium hydride was slowly added and the mixture was stirred for 15 minutes. Methanesulfonyl chloride (66 μl, 0.85 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction was extracted with ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue (200 mg) was used in the next synthetic step without further purification.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionThe reaction was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue (200 mg) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-b1f9264ae34944eabffc0927136c110e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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