Water → 1-(Benzenesulfonyl)-3-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1049385Notes

Reaction equation

HRID 1049385 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][N:13]=2.O>CN(C=O)C>[Br:8][C:18]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:20])=[O:21])[C:10]=1[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 12363722-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 111523201-(Benzenesulfonyl)-3-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

25 g of NBS in 75 ml of DMF are added to a solution of 34.8 g of 2-methyl-1-(benzenesulfonyl)-7-azaindole in 75 ml of DMF. The mixture is stirred at room temperature for 1 h, poured into water, the precipitate which has precipitated out is separated off, washed with water and dried, giving 42 g of 3-bromo-2-methyl-1-(benzenesulfonyl)-7-azaindole, M˜351.22 g/mol, M+H found 351.

Workup

  1. customthe precipitate which has precipitated out
  2. customis separated off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-651a014dff0845afa325c3b643a2d9c9
Source dataset
uspto-grants-2016_07
Patent number
US09382244B2

Reaction notes

Loading…