Water → 2-[4-(4-Pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-quinoline

HRID 1170323Notes

Reaction equation

HRID 1170323 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[N:10][N:9]=[C:8]2[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1.O>CN(C)C=O>[N:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH:11]=[N:10][N:9]=[C:8]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 1363758244-(4-Pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-phenol

Product 1

HCID 116105772-[4-(4-Pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-quinolineYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(4-Pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-phenol (44 mg) in dimethyl formamide (1 ml) in a 7 ml Teflon capped vial was added cesium carbonate (185 mg) and 2-Chloromethyl-quinoline (37 mg) and the reaction mixture heated on a shaker plate at 60° C. for 18 h. The reaction mixture was poured into water and extracted with methylene chloride, dried magnesium sulfate, filtered and concentrated to provide the title compound (45 mg). 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.65 (d, J=6.0 Hz, 2H), 8.37 (d, J=8.3 Hz, 1H), 8.03 (d, J=8.7 Hz, 1H), 7.94 (d, J=7.9 Hz, 1H), 7.78 (m, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.61 (t, J=5.8 Hz, 1H), 7.40 (m, 4H), 7.14 (d, J=9.1 Hz, 2H), 5.38 (s, 2H); MS: (M+H m/z=380.2).

Workup

  1. extractionextracted with methylene chloride, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6b8d6a9659964741a7958a04f6812456
Source dataset
uspto-grants-2010_11
Patent number
US07825254B2

Reaction notes

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