Sodium Methoxide → 4-{5-[2-Methoxy-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

HRID 1497791Notes

Reaction equation

HRID 1497791 reaction equation
Cl[C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.[CH3:35][O-:36].[Na+]>CO>[CH3:35][O:36][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 867081054-{5-[2-Chloro-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

Product 1

HCID 730520794-{5-[2-Methoxy-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrileYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A cloudy solution of 4-{5-[2-chloro-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Int. 19, 22 mg, 0.046 mmol) and NaOMe (25% Wt, 0.75 mL, 3.3 mmol) in MeOH (0.75 mL) was heated at 100° C. for 30 mins using microwave irradiation. The cooled reaction mixture was evaporated in vacuo preparative TLC (20×20 cm×1 mm) eluting with 50% EtOAc in cyclohexane to give the title compound as a white solid (6 mg).

Workup

  1. custommicrowave irradiation
  2. customThe cooled reaction mixture
  3. customwas evaporated in vacuo preparative TLC (20×20 cm×1 mm)
  4. washeluting with 50% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-a513bb3ee8174f698f242972193ed4dc
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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