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

HRID 2426857
Notes
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Reaction equation

HRID 2426857 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=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>[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=3)(=[O:20])=[O:19])[C:5]2=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497588891H-Pyrrolo[2,3-B]pyridine, 5-fluoro-1-[(4-methylphenyl)sulfonyl]-Yield 78.5%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfate
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.3 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine, 3.54 g of 4-methylbenzenesulfonyl chloride, 7.56 g of sodium hydroxide dissolved in 55 ml of water, and 0.115 g of tetrabutylammonium hydrogen sulfate in 125 ml of toluene is agitated at around 20° C. for approximately 24 hours. The mixture is diluted with 500 ml of ethyl acetate; the organic phase is washed with three times 200 ml 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 silica column [eluent: dichloromethane]. 3.85 g of 5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. washthe organic phase is washed with three times 200 ml 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 silica column [eluent: dichloromethane]

Sources & evidence

ORD record
ord-ec9abf30aa29452484d5de9b89a19bc1
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968566B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes