4-Toluenesulfonyl chloride → HCID 71240463, compound

HRID 80743Notes

Reaction equation

HRID 80743 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].[NH4+].[Cl-]>C1COCC1>[Br:3][C:4]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 225669164-Bromo-5-isopropyl-1H-indazole

Product 1

HCID 71240463HCID 71240463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 241 mg, 6.02 mmol) was added to a solution of 4-bromo-5-isopropyl-1H-indazole (720 mg, 3.01 mmol) in THF (15 mL) at 0° C. After 10 min, TsCl (861 mg, 4.52 mmol) was added and the resulting mixture was stirred at 0° C. for 1 h, then at room temperature overnight. Saturated aqueous NH4Cl was added and the mixture was extracted with EtOAc (2×). The combined organics were washed with brine, dried (Na2SO4) and concentrated. Ther residue was purified by silica gel chromatography (0-30% EtOAc/heptanes) to provide 4-bromo-5-isopropyl-1-tosyl-1H-indazole. MS (ESI+) m/z 394.8 (M+H)+.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customTher residue was purified by silica gel chromatography (0-30% EtOAc/heptanes)

Sources & evidence

ORD record
ord-ebbfc79b2ee94487a105aa8641ff31be
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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