4-Toluenesulfonyl chloride → HCID 87550393, compound

HRID 1895975Notes

Reaction equation

HRID 1895975 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([S:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH2:15][CH2:16]2)[N:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87550393HCID 87550393, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the Compound of Example 3 (60 mg, 0.283 mmol), p-toluenesulfonyl chloride (80.9 mg, 0.425 mmol), TEA (0.425 mmol) in 5 mL of CHCl3 was stirred at r.t. for 1 h. The chloroform solution was washed with NaOH 0.1 N, water, dried over Na2SO4 and evaporated to dryness in vacuo. Purification by flash chromatography (EtOAc—Petroleum Ether 1:1), afforded 67 mg of the title product.

Workup

  1. washThe chloroform solution was washed with NaOH 0.1 N, water
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness in vacuo
  4. customPurification by flash chromatography (EtOAc—Petroleum Ether 1:1)

Sources & evidence

ORD record
ord-53b8481cc815436f9b84f8e03df66203
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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