氰化钾 → (s)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-6-yl]-acetonitrile

HRID 8279

反应方程式

HRID 8279 反应方程式
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:14][N:13]3[C@H:23]([CH2:26]OS(C)(=O)=O)[CH2:24][CH2:25][C:12]=23)=[CH:7][CH:6]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C(OCC)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:14][N:13]3[C@H:23]([CH2:26][C:1]#[N:2])[CH2:24][CH2:25][C:12]=23)=[CH:7][CH:6]=1

参与物

7

反应物 2

HCID 9032氰化钾HCID 87799512(S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester

产物 1

HCID 9902141(s)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-6-yl]-acetonitrile

试剂、催化剂与溶剂 4

HCID 67553四丁基碘化铵催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
70 °C

实验过程

A mixture of potassium cyanide (44 mg, 0.67 mmol), tetrabutylammonium iodide (catalytic), and (S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester (54 mg, 0.135 mmol) in N,N-dimethylformamide (0.35 mL) and water (0.13 mL) is heated at 70° C. for 4 h. The mixture is cooled, taken up in ethyl acetate (20 mL), washed with water and brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (2% methanol/chloroform) to yield the title compound, 25 mg (56%).

后处理

  1. temperatureThe mixture is cooled
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (2% methanol/chloroform)

来源与证据

ORD记录
ord-5b953fa7674c4f19b380bf9e67c072b5
来源数据集
uspto-grants-2006_08
专利号
US07087626B2

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