tert-Butanol → 4-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

HRID 625315Notes

Reaction equation

HRID 625315 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=[CH:11][C:10]=2[N+:21]([O-:23])=[O:22])[CH:4]=1)#[CH:2].[CH2:24]([N:31]=[N+:32]=[N-:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].C(O)(C)(C)C>[O-]S([O-])(=O)=O.[Cu+2].O>[CH2:24]([N:31]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([C:9]3[CH:14]=[C:13]([N:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[CH:12]=[CH:11][C:10]=3[N+:21]([O-:23])=[O:22])[CH:4]=2)[N:33]=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 867059454-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

Product 1

HCID 867059464-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

A solution of 50 mg of 4-ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine, 20 μL of benzyl azide, 16.3 μL of 1 M aqueous sodium ascorbate solution, 5.4 μL of 0.3 M CuSO4 solution, 326 μL of tert-butanol, and 326 μL of water was stirred for 2 days and then the solvent was evaporated at reduced pressure. The residue was dissolved in dichloromethane. The solution was washed with water and dried. The solvent was evaporated at reduced pressure and the residue was chromatographed on silica gel eluting with a 0% to 4% gradient of methanol in dichloromethane. The process yielded 22 mg of product.

Workup

  1. customthe solvent was evaporated at reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washThe solution was washed with water
  4. customdried
  5. customThe solvent was evaporated at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with a 0% to 4% gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-2a7f511b2b1d495d926d44fda02ea020
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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