Water → 2-(4-Chloro-phenyl)-6-[4-(4-[1,2,3]triazol-1-yl-butyl)-phenoxymethyl]-pyridine

HRID 33526Notes

Reaction equation

HRID 33526 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:22]=1.O>CN(C)C=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[N:22]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 691065802-Chloromethyl-6-(4-chloro-phenyl)-pyridine

Product 1

HCID 160657162-(4-Chloro-phenyl)-6-[4-(4-[1,2,3]triazol-1-yl-butyl)-phenoxymethyl]-pyridineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 89 mg (0.42 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)phenol in 4.0 ml N,N-dimethylformamide was treated at 0° C. with 17 mg (0.42 mmol) of 60% sodium hydride and stirred at 0° C. for 30 min. Then 100 mg (0.42 mmol) 2-Chloromethyl-6-(4-chloro-phenyl)-pyridine [ZA 6706809] were added and stirred continued at r.t. over night. After addition of 8 ml water, the precipitate was isolated, washed thoroughly with water and n-heptane. The residue was dried at 40° C. and purified by LC-MS to give 80.5 mg (47%) of the title compound as white powder.

Workup

  1. stirringstirred
  2. waitcontinued at r.t. over night
  3. customthe precipitate was isolated
  4. washwashed thoroughly with water and n-heptane
  5. customThe residue was dried at 40° C.
  6. custompurified by LC-MS

Sources & evidence

ORD record
ord-b5bf564d537042678e19bf607b976f0d
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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