Water → HCID 18404041, compound

HRID 1017632Notes

Reaction equation

HRID 1017632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][C:14]([OH:18])=[C:15]([Br:17])[CH:16]=[C:11]2[N:10]=[N:9]1.[CH3:19][N:20]1[C:24]([CH2:25]Cl)=[N:23][CH:22]=[N:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][C:14]([O:18][CH2:25][C:24]3[N:20]([CH3:19])[N:21]=[CH:22][N:23]=3)=[C:15]([Br:17])[CH:16]=[C:11]2[N:10]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 104192195-(Chloromethyl)-1-methyl-1H-1,2,4-triazoleHCID 178516986HCID 178516986, compound

Product 1

HCID 18404041HCID 18404041, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-fluorophenyl)-5-hydroxy-6-bromo-1,2,3-triazolo[4,5-b]pyridine (0.91 g, 2.94 mmol), 2-methyl-3-chloromethyl-1,2,4-triazole (0.46 g, 3.53 mmol) and caesium carbonate (1.40 g, 4.29 mmol) in dry DMF (15 ml) was stirred at room temperature under nitrogen for 18 h. The mixture was poured into water (150 ml) and extracted with ethyl acetate (2×100 ml). The extracts were dried (Na2SO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 4% methanol-dichloromethane, gave 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-bromo-1,2,3-triazolo[4,5-b]pyridine (1.05 g, 88%) as a beige solid. δH (360 MHz; CDCl3) 3.96 (3H, s), 5.59 (2H, s), 7.37-7.43 (2H, m), 7.56-7.64 (1H, m), 7.68 (1H, dd, J=7 and 7), 7.87 (1H, s) and 8.62 (1H, s); m/z (ES+) 404, 406 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washFlash column chromatography on silica gel, eluting with 4% methanol-dichloromethane

Sources & evidence

ORD record
ord-ddd157375b9d45d887befe68e0e9e723
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

Loading…