4-Toluenesulfonyl chloride → HCID 59699753, compound

HRID 901510Notes

Reaction equation

HRID 901510 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.[OH-:29].[K+].[OH-:31].C([N+]([CH2:45][CH2:46][CH2:47][CH3:48])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.[Br-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][S:24]([C:21]4[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=4)(=[O:26])=[O:25])=[CH:13][CH:12]=3)=[CH:9][N:8]([S:24]([C:21]3[CH:45]=[CH:46][C:47]([CH3:48])=[CH:19][CH:20]=3)(=[O:31])=[O:29])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 59699729HCID 59699729, compound

Product 1

HCID 59699753HCID 59699753, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 253881Sodium BromideSolvent

Procedure

2.82 g (9.75 mmol) of 4-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-phenol and 3.10 g of para-toluenesulfonyl chloride were dispersed in 400 ml of toluene at 45° C. 45 ml of 50% aqueous solution of KOH and 1.5 ml of 40% aqueous solution of tetra-n-butylammonium hydroxide were added and the resulting mixture stirred vigorously at ambient temperature for 6 h. The resulting mixture was diluted with 100 ml of a saturated aqueous solution of sodium bromide, the phases separated and the aqueous layer extracted three times with toluene. The combined organic phases were washed with a 2 M aqueous solution of sodium hydroxide, dried over sodium sulfate and evaporated. The crude was crystallized from ethanol containing 10% v/v of toluene to afford 3.22 g (5.29 mmol, 55% yield) of toluene-4-sulfonic acid 4-[5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]-phenyl ester as ivory crystalline needles.

Workup

  1. customthe phases separated
  2. extractionthe aqueous layer extracted three times with toluene
  3. washThe combined organic phases were washed with a 2 M aqueous solution of sodium hydroxide
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude was crystallized from ethanol containing 10% v/v of toluene

Sources & evidence

ORD record
ord-c0514154357c4c6f85dab96c51d4904f
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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