Pyridine → HCID 74017985, compound

HRID 1170855Notes

Reaction equation

HRID 1170855 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]1([N:18]2[C:26]3[CH2:25][CH2:24][CH2:23]/[C:22](=[CH:27]\[CH2:28][OH:29])/[C:21]=3[CH:20]=[N:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:2]1([CH3:1])[CH:7]=[CH:6][C:5]([S:8]([O-:10])(=[O:29])=[O:9])=[CH:4][CH:3]=1.[C:12]1([N:18]2[C:26]3[CH2:25][CH2:24][CH2:23][C:22](=[CH:27][CH2:28][N+:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:21]=3[CH:20]=[N:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 58978939HCID 58978939, compound

Product 1

HCID 74017985HCID 74017985, compoundYield 60%

Conditions

Temperature
0 °C

Procedure

P-toluenesulfonyl chloride (210 mg, 1.10 mmol) is added to a solution of (E)-2-(6,7-dihydro-1-phenyl-1H-indazol-4(5H)-ylidene)etanol (254 mg, 1.05 mmol) in 10 mL de pyridine cooled to a 0° C. The reaction is followed up by TLC. Next, the solvent is evaporated, the crude is diluted with CHCl3, and washed with a diluted solution of NaHCO3. The organic phase is evaporated at reduced pressure, to obtain 1-[2-(1-phenyl-1,5,6,7-tetrahydroindazol-4-ylidene)-ethyl]-pyridinium toluene-4-sulfonate (300 mg, 0.63 mmol, 60%, yellow solid).

Workup

  1. customNext, the solvent is evaporated
  2. additionthe crude is diluted with CHCl3
  3. washwashed with a diluted solution of NaHCO3
  4. customThe organic phase is evaporated at reduced pressure

Sources & evidence

ORD record
ord-5e0f3d96f8c94615969578a5e82bc150
Source dataset
uspto-grants-2010_11
Patent number
US07829559B2

Reaction notes

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