Water → HCID 57377473, compound

HRID 1258916Notes

Reaction equation

HRID 1258916 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[N:14]=[CH:15][NH:16][CH:17]=3)=[C:11]([CH3:18])[N:10]=[N:9]2)=[CH:4][CH:3]=1.Cl[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:20]4[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=4)[CH:17]=3)=[C:11]([CH3:18])[N:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 178434695HCID 178434695, compound

Product 1

HCID 57377473HCID 57377473, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(4-fluoro-phenyl)-5-(1H-imidazol-4-yl)-4-methyl-1H-[1,2,3]triazole (500 mg, 2.06 mmol), methyl 6-chloronicotinate (353 mg, 2.06 mmol) and potassium carbonate (568 mg, 4.11 mmol) in DMF (10 mL) was stirred under Ar in a sealed flask and heated at 120° C. for 16 h. After cooling to room temperature the mixture was poured into water (150 mL) and the solid that formed was filtered off and dried to afford the title compound (300 mg, 39%) as a light brown solid. MS: m/e=379.3 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customthe solid that formed
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-0ad44bd4de5e4ba6b8221000ba3498b9
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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