Cesium carbonate → 6-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine

HRID 1017637Notes

Reaction equation

HRID 1017637 reaction equation
[C:1]1([N:7]2[C:11]3[NH:12][C:13](=[O:20])[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:15][C:10]=3[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:22][N:23]1[C:27]([CH2:28]Cl)=[N:26][CH:25]=[N:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:18][C:16]([C:14]1[CH:15]=[C:10]2[N:9]=[N:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]2=[N:12][C:13]=1[O:20][CH2:28][C:27]1[N:23]([CH3:22])[N:24]=[CH:25][N:26]=1)([CH3:17])[CH3:19]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochlorideHCID 1358341243-Phenyl-6-(tert-butyl)-3,4-dihydro-1,2,3-triazolo[4,5-b]pyridin-5-one

Product 1

HCID 98204146-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridineYield 83%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-phenyl-6-(tert-butyl)-3,4-dihydro-1,2,3-triazolo[4,5-b]pyridin-5-one (0.025 g, 0.093 g), 2-methyl-3-chloromethyl-1,2,4-triazole hydrochloride (0.15 g, 1.1 mmol) and cesium carbonate (0.65 g, 2.0 mmol) in dry DMF (4 ml) was stirred at r.t. for 20 h. The mixture was diluted with water (50 ml) and 1M citric acid (5 ml), and extracted with dichloromethane (2×25 ml). The extracts were dried (Na2SO4), filtered and concentrated. Preparative thin-layer chromatography, eluting with 5% methanol-dichloromethane, gave 6-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine (0.028 g, 83%) as a white solid, m.p. 165-167° C. δH (360 MHz; CDCl3) 1.43 (9H, s), 3.94 (3H, s), 5.69 (2H, s), 7.46 (1H, t, J=7), 7.60 (2H, dd, J=7 and 7), 7.93 (1H, s), 8.20 (2H, d, J=7) and 8.31 (1H, s); m/z (ES+) 364 (M+H+).

Workup

  1. extractionextracted with dichloromethane (2×25 ml)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washPreparative thin-layer chromatography, eluting with 5% methanol-dichloromethane

Sources & evidence

ORD record
ord-6f053d8340df402193106a5f7144975d
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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