三乙胺 → N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide

HRID 1870490

反应方程式

HRID 1870490 反应方程式
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:11]([OH:13])=O)[C:3]1=2.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=O.CO[C:29]1C=C[C:32]([NH2:35])=[CH:31][N:30]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:22][O:24][C:25]1[CH:26]=[CH:29][N:30]=[CH:31][C:32]=1[NH:35][C:11]([C:4]1[C:3]2[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=2[NH:6][CH:5]=1)=[O:13]

参与物

7

反应物 5

HCID 8471三乙胺HCID 10928氯甲酸乙酯HCID 25517氯化铵HCID 811215-氨基-2-甲氧基吡啶HCID 153376324-氧-4,5,6,7-四氢-1H-吲哚-3-羧酸

产物 1

HCID 18696549N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide收率 19.6%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂2 次

实验过程

To a stirring solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol) and triethylamine (293 μl, 2.1 mmol) in N,N-dimethylformamide (3 mL) at 0° C. was added ethyl chloroformate (191 μl, 2 mmol). After stirring an additional 30 minutes, a solution of 2-methoxy-5-amino-pyridine (216 mg, 2 mmol) in N,N-dimethylformamide (3 mL) was added. The reaction mixture was allowed to stir for an additional 75 minutes, then poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated in vacua. To the residue was added aqueous 5N sodium hydroxide (5 mL) and ethyl alcohol (1 mL), then heated at reflux for 1 hour. After cooling in an ice water bath, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacua, and the residue recrystallized from ethyl acetate to give N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide (56 mg); m. p. 209-210° C. (Compound 1).

后处理

  1. stirringto stir for an additional 75 minutes
  2. extractionextracted 2× with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacua
  7. additionTo the residue was added aqueous 5N sodium hydroxide (5 mL) and ethyl alcohol (1 mL)
  8. temperatureheated
  9. temperatureat reflux for 1 hour
  10. temperatureAfter cooling in an ice water bath
  11. additionthe reaction mixture was poured into saturated aqueous ammonium chloride
  12. extractionextracted 2× with ethyl acetate
  13. dry with materialThe combined organic layers were dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacua
  16. customthe residue recrystallized from ethyl acetate

来源与证据

ORD记录
ord-3e38bf07d7904bc08b04577813a18035
来源数据集
uspto-grants-2000_08
专利号
US06096887

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