p-Toluenesulfonyl azide → HCID 66636686, compound

HRID 1094324Notes

Reaction equation

HRID 1094324 reaction equation
[CH3:1][C@@H:2]([C:5]1[CH:20]=[CH:19][C:8]([CH2:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)=[CH:7][CH:6]=1)[C:3]#[CH:4].[C:21]1([CH3:33])[CH:26]=[CH:25][C:24]([S:27]([N:30]=[N+:31]=[N-:32])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl.[Cu]I>[CH3:33][C:21]1[CH:22]=[CH:23][C:24]([S:27]([N:30]2[CH:4]=[C:3]([C@@H:2]([C:5]3[CH:6]=[CH:7][C:8]([CH2:9][C:10]4[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=4)=[CH:19][CH:20]=3)[CH3:1])[N:32]=[N:31]2)(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 13661p-Toluenesulfonyl azideHCID 86645976HCID 86645976, compound

Product 1

HCID 66636686HCID 66636686, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6212ChloroformSolvent

Procedure

A cooled (0-5° C.) mixture of 2-{4-[(1R)-1-methylprop-2-yn-1-yl]benzyl}-4-(trifluoromethyl)-1,3-thiazole (0.115 g, 0.4 mmol), p-toluenesulfonylazide (66 mg, 0.33 mmol), 2,6-toluidine (48 mg, 0.4 mmol) and CuI (5% mmol) in CHCl3 (5 ml) was stirred for 12 h. The reaction was quenched by adding a buffer solution (pH=5.4) and the product extracted with CHCl3 (3×5 ml). After solvent evaporation the crude was purified by flash chromatography to give pure 1-(4-methylbenzensulfonyl)-4-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl}phenyl)ethyl]-1H-1,2,3-triazole (0.95 g, 0.20 mmol) as a yellow oil (50%).

Workup

  1. temperatureA cooled
  2. customThe reaction was quenched
  3. additionby adding a buffer solution (pH=5.4)
  4. extractionthe product extracted with CHCl3 (3×5 ml)
  5. customAfter solvent evaporation the crude
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ab2b3616ec054048bea48be512059445
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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