4-Toluenesulfonyl chloride → HCID 59700039, compound

HRID 729805Notes

Reaction equation

HRID 729805 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[NH:12][N:13]=[CH:14][CH:15]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-:16].C([N+]([CH2:30][CH2:31][CH2:32][CH3:33])(CCCC)CCCC)CCC.[OH-:34].[K+].[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]([S:42]([C:39]4[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=4)(=[O:44])=[O:43])[N:13]=[CH:14][CH:15]=3)=[CH:9][N:8]([S:42]([C:39]3[CH:30]=[CH:31][C:32]([CH3:33])=[CH:37][CH:38]=3)(=[O:34])=[O:16])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 135983719HCID 135983719, compound

Product 1

HCID 59700039HCID 59700039, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-3-(2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine (1.51 g, 5.75 mmol) in toluene (5 mL) was added tetrabutylammonium hydroxide (40% wt in H2O, 285 uL) and a 50% KOH (aq) solution (5.7 mL). The reaction mixture was stirred for 20 minutes at ambient temperature and para-toluenesulfonylchloride (2.17 g, 11.50 mmol) was added. The reaction was stirred at ambient temperature for 2.5 hours. The product was extracted into ethyl acetate and the organic layer was washed with H2O then dried over Na2SO4. The material was concentrated under vacuum and adsorbed onto silica gel. Purification by flash chromatography on silica gel with a gradient of ethyl acetate and hexane afforded the title compound as a yellow solid (1.73 g, 53% yield). 1H NMR (500 MHz, d6-DMSO) δ 8.68 (s, 1H), 8.57 (d, J=2.5 Hz, 1H), 8.54 (d, J=2.5 Hz, 1H), 8.49 (d, J=2.5 Hz, 1H), 7.96 (d, J=9 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 7.47 (d, J=8.5 Hz, 2H), 7.41 (d, J=8 Hz, 2H), 7.29 (d, J=3 Hz, 1H), 2.36 (s, 3H), 2.32 (s, 3H). MS: m/z 570.9/571.9 (M+H+).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 2.5 hours
  2. extractionThe product was extracted into ethyl acetate
  3. washthe organic layer was washed with H2O
  4. dry with materialthen dried over Na2SO4
  5. concentrationThe material was concentrated under vacuum
  6. customPurification by flash chromatography on silica gel with a gradient of ethyl acetate and hexane

Sources & evidence

ORD record
ord-59b0a207f9ff425d9593a85181d531a7
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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