Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

HRID 1641481Notes

Reaction equation

HRID 1641481 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.[OH-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:9]=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-1H-pyrrolo[2,3-b]pyridine (6.9 g, prepared according to the method described in Organic Letters, 2003, vol. 5, 5023-5025) and benzyltriethylammonium chloride (210 mg) in methylene chloride (150 mL), sodium hydroxide (4.3 g) and benzenesulfonyl chloride (5.5 mL) were added under ice-cooling. The reaction mixture was stirred at room temperature for 1 hour and filtered through “Celite” (registered trademark), and the filtrate was concentrated. The resulting residue was purified by a purification system CombiFlash CompanionXL (manufactured by Isco, Co., Ltd., column: RediSep 120 g; hexane:ethyl acetate=95:5→60:40) to obtain the title compound (9.8 g) having the following physical properties.

Workup

  1. additionwere added under ice-
  2. temperaturecooling
  3. filtrationfiltered through “Celite” (registered trademark)
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by a purification system CombiFlash CompanionXL (manufactured by Isco, Co., Ltd., column: RediSep 120 g; hexane:ethyl acetate=95:5→60:40)

Sources & evidence

ORD record
ord-fddc36a378ce4d1380f07a9c2cd2acbf
Source dataset
uspto-grants-2012_02
Patent number
US08115014B2

Reaction notes

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