Triethylamine → 6-Methyl-2-(4-methylphenyl)-alpha-oxo-imidazo[1,2-a]pyridine-3-acetic Acid Ethyl Ester

HRID 1934881

반응식

HRID 1934881 반응식
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([O-:4])=O.[K+].P(Cl)(Cl)(Cl)=O.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]3[CH:31]=2)=[CH:18][CH:17]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:23]=[C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]3[C:31]=2[C:2](=[O:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])=[CH:20][CH:21]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 6677206-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridineHCID 23678856Ethanedioic acid, 1-ethyl ester, potassium salt (1:1)

생성물 1

HCID 111630496-Methyl-2-(4-methylphenyl)-alpha-oxo-imidazo[1,2-a]pyridine-3-acetic Acid Ethyl Ester수율 97.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
10 °C

실험 절차

A suspension of potassium monoethyl oxalate (84.3 g; 0.54 mols) in methylene chloride (395 mL) is added dropwise with phosphorous oxychloride (82.8 g; 0.54 mols) keeping the temperature at about 30° C. After 4÷6 hours, 2-(4-methylphenyl)-6-methylimidazo[1,2-a]-pyridine (100.0 g; 0.45 mols) is added, keeping the temperature below 35° C. The resulting suspension is added dropwise with triethylamine (50.5 g; 0.50 mols) keeping the mixture at the reflux temperature. After one hour under these conditions, the reaction mixture is cooled to 5÷10° C. and poured into a suspension of sodium carbonate (95 g; 0.89 mols) in water (500 mL) keeping the temperature below 35° C. The phases are separated and the upper aqueous phase is reextracted with methylene chloride (45 mL). The combined organic phases are washed with water (45 mL) and concentrated to a residue under vacuum. The solid residue is taken up in ethanol (590 mL), heated to dissolution and left to crystallize. After cooling to about 0° C. the solid is filtered, washed with ethanol and dried at 50° C. under vacuum to obtain ethyl 2-(4-methylphenyl)-6-methylimidazo[1,2-a]-pyridine-3-glyoxalate (141.5 g, 99.5% titre, 97.5% yield).

후처리

  1. customat about 30° C
  2. customthe temperature below 35° C
  3. customthe temperature below 35° C
  4. customThe phases are separated
  5. washThe combined organic phases are washed with water (45 mL)
  6. concentrationconcentrated to a residue under vacuum
  7. temperatureheated to dissolution
  8. waitleft
  9. customto crystallize
  10. temperatureAfter cooling to about 0° C. the solid
  11. filtrationis filtered
  12. washwashed with ethanol
  13. customdried at 50° C. under vacuum

출처 및 근거

ORD 기록
ord-6bb3a72d10644d1bb2b0ce6f5a1e9f72
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384226B2

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