4-Toluenesulfonyl chloride → 1H-Pyrrolo[2,3-B]pyridine, 4-chloro-5-fluoro-1-[(4-methylphenyl)sulfonyl]-

HRID 2426895Notes

Reaction equation

HRID 2426895 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[CH:10]=[CH:11][C:3]=12

Participants

8

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 497588981H-Pyrrolo[2,3-B]pyridine, 4-chloro-5-fluoro-1-[(4-methylphenyl)sulfonyl]-Yield 76.8%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.30 g of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, 1.6 g of 4-methylbenzenesulfonyl chloride, 3.40 g of sodium hydroxide dissolved in 16 cm3 of water, and 0.052 g of tetrabutylammonium hydrogen sulfate in 200 cm3 of toluene is stirred for about 24 hours in the region of 20° C. The mixture is diluted with 500 cm3 of ethyl acetate; the organic phase is washed with three times 200 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a column of silica [eluent: dichloromethane]. 1.90 g of 4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are thus obtained in the form of a powder, the characteristics of which are as follows:

Workup

  1. washthe organic phase is washed with three times 200 cm3 of water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  5. customThe residue is purified by flash chromatography on a column of silica [eluent: dichloromethane]

Sources & evidence

ORD record
ord-f407b6f1bddb4712a3e34da9bdc74d6f
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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