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

HRID 402417노트

반응식

HRID 402417 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 7918Acetic Anhydride용매

반응 조건

온도
120 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-457d714349f746aaaf067e8c375b82a1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742097B2

반응 노트

불러오는 중…