N,N-二甲基甲酰胺 → HCID 66772244，化合物

HRID 1645260

反应方程式

HRID 1645260 反应方程式
O=P(Cl)(Cl)Cl.[CH3:6][N:7]([CH:9]=[O:10])C.[CH3:11][C:12]1[CH:16]=[CH:15][O:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].N1C2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][C:24]1=O.N1CCCCC1>CCO.O>[CH3:11][C:12]1[CH:16]=[CH:15][O:14][C:13]=1[CH:30]=[C:29]1[C:28]2[C:6](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:7][C:9]1=[O:10]

参与物

9

反应物 6

HCID 6228N,N-二甲基甲酰胺HCID 8082六氢吡啶HCID 10340Carbonic acid sodium salt (1:2)HCID 135873-甲基呋喃HCID 24813三氯氧磷HCID 3217102-吲哚酮

产物 1

HCID 66772244HCID 66772244，化合物收率 25.3%

试剂、催化剂与溶剂 2

HCID 702乙醇溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
0 °C

实验过程

A solution of POCl3 (0.60 mL, 7.08 mmol) in DMF (0.65 mL, 8.431 mmol) was stirred at rt for 1 h. The reaction was cooled to 0° C. and added 3-methylfuran (490 mg, 5.97 mmol) dropwise. The mixture was stirred at 0 C for 1 h and at 40 C for additional 40 min. The reaction mixture was poured into H2O (25 mL), neutralized (Na2CO3), and extracted with EtOAc (25 mL×5). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude material was heated at reflux with oxindole (800 mg, 6.02 mmol) and piperidine (0.60 mL, 8.08 mmol) in EtOH (5 mL) for 3 h. The resulting precipitate was collected by filtration to yield the desired 3-((3-methylfuran-2-yl)methylene)indolin-2-one (340 mg). LCMS (ES): m/z 226 [M+1]+.

后处理

  1. extractionextracted with EtOAc (25 mL×5)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. temperatureThe crude material was heated
  6. filtrationThe resulting precipitate was collected by filtration

来源与证据

ORD记录
ord-dfff84b0d0214ac1b9cce94e054bf1f8
来源数据集
uspto-grants-2012_02
专利号
US08124649B2

关联笔记

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