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

HRID 402417ノート

反応式

HRID 402417 の反応式
[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

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 231548Methyl 6-methylnicotinateHCID 866647645-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazole-4-carbaldehyde

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 7918Acetic Anhydride溶媒

反応条件

温度
120 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-457d714349f746aaaf067e8c375b82a1
出典データセット
uspto-grants-2014_06
特許番号
US08742097B2

反応ノート

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