1H-1,2,4-Triazole → HCID 90415592, compound

HRID 578839Notes

Reaction equation

HRID 578839 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:18])=[N:5][C:6]([O:16][CH3:17])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH:8]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Cl:15][C:11]1[CH:10]=[C:9]([C:7]2[C:6]([O:16][CH3:17])=[N:5][C:4]([CH3:18])=[C:3]([CH2:2][N:19]3[CH:23]=[N:22][CH:21]=[N:20]3)[CH:8]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 90414955HCID 90414955, compound2×

Product 1

HCID 90415592HCID 90415592, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(chloromethyl)-5-(3-chlorophenyl)-6-methoxy-2-methylpyridine (Intermediate 8, 87 mg, 0.31 mmol), in acetone (12 mL), was added 1H-1,2,4-triazole (32 mg, 0.46 mmol), and cesium carbonate (150 mg, 0.63 mmol). The reaction mixture stirred at room temperature for 2 h, then filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 0-100%, EtOAc/hexanes) afforded the title compound (82.4 mg, 84%). 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.98 (s, 1H), 7.52 (s, 1H), 7.45-7.37 (m, 2H), 7.37-7.29 (m, 2H), 5.34 (s, 2H), 3.98 (s, 3H), 2.52 (s, 3H). [M+H]=315.22.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customPurification (FCC, SiO2, 0-100%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-95d6706a60a04ab4aefd266afb2c6d3f
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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