Sodium hydride → 5-Bromo-1-(methylsulfonyl)indoline

HRID 2360046Notes

Reaction equation

HRID 2360046 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:14]([CH3:13])(=[O:16])=[O:15])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 34115665-Bromoindoline

Product 1

HCID 5759865-Bromo-1-(methylsulfonyl)indolineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To DMF (5.0 ml) was added sodium hydride (53 mg, 1.3 mmol) and the solution stirred at room temperature for 30 min. 5-Bromoindoline (240 mg, 1.2 mmol) was added and the solution was stirred at room temperature for 30 min. Methanesulfonyl chloride (94 ul, 1.2 mmol) was added and the solution stirred at room temperature overnight, then concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 2% CH3OH/CHCl3 to give the title compound (202 mg, 60%).

Workup

  1. stirringthe solution was stirred at room temperature for 30 min
  2. stirringthe solution stirred at room temperature overnight
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel eluting with 2% CH3OH/CHCl3

Sources & evidence

ORD record
ord-607a0df6893f4fd2a3bf3fa295a6fda7
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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