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

HRID 1006663ノート

反応式

HRID 1006663 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒2 回

反応条件

温度
2.5 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2ae01a938c03425085f6257ded584db3
出典データセット
uspto-grants-2004_09
特許番号
US06790960B2

反応ノート

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