Water → 6-{(E)-2-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-vinyl}-nicotinic acid methyl ester

HRID 402417Notes

Reaction equation

HRID 402417 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[N:21][CH:20]=1.O.[OH-].[Na+]>C(OC(=O)C)(=O)C.CC(O)=O>[CH3:16][O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:14]/[C:9]2[N:10]([CH3:13])[N:11]=[N:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 231548Methyl 6-methylnicotinateHCID 86664764HCID 86664764, compound

Product 1

HCID 573352596-{(E)-2-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-vinyl}-nicotinic acid methyl esterYield 30.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carbaldehyde (308 mg, 1.5 mmol) in acetic anhydride (0.8 mL) and AcOH (141 μL) was added methyl-6-methylnicotinate (227 mg, 1.5 mmol) and the reaction mixture was heated at 120° C. for 144 h. The mixture was then poured into water, sodium hydroxide (2 N) added and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 10% methanol in dichloromethane) afforded the title compound (154 mg, 30%) as a light brown solid. MS: m/e=339.1 [M+H]+.

Workup

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-457d714349f746aaaf067e8c375b82a1
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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