Sodium Hydroxide → 8-(4-Methoxy-2,6-dimethylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1006663노트

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HRID 1006663 반응식
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:18]([CH:19]=O)=[C:17]([CH3:24])[CH:16]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:18]([CH2:19][NH:1][C:2]2[C:3]3[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[C:17]([CH3:24])[CH:16]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 8167794-Methoxy-2,6-dimethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

생성물 1

HCID 98396428-(4-Methoxy-2,6-dimethylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine수율 60.5%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매2회

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온도
2.5 °C

실험 절차

8-amino-2,3-dimethylimidazo[1,2-a]pyridine (0.5 g, 3.1 mmol), 4-methoxy-2.6-dimethylbenzaldehyd (0.51 g, 3.11 mmol) were dissolved in methanol (10 ml) whereupon zinc chloride (0.51 g, 3.82 mmol) dissolved in methanol (5 ml) was added. Sodium cyanoborohydride was added in portions and the mixture was refluxed for 3 h under under nitrogen. The mixture was stirred at 0-5° C. and 1 M sodium hydroxide (20 ml) was added. After extraction with 2×50 ml of methylene chloride the combined organic layer was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on silica (dichloromethane: ethyl acetate, 1:1) yielding 0.58 g 60% of the title compound.

후처리

  1. additionwas added
  2. temperaturethe mixture was refluxed for 3 h under under nitrogen
  3. extractionAfter extraction with 2×50 ml of methylene chloride the combined organic layer
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was chromatographed on silica (dichloromethane: ethyl acetate, 1:1)

출처 및 근거

ORD 기록
ord-2ae01a938c03425085f6257ded584db3
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790960B2

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