乙二醇二甲醚 → 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

HRID 15987

反应方程式

HRID 15987 反应方程式
COCCOC.C([O-])([O-])=O.[Na+].[Na+].Br[C:14]1[N:19]=[C:18]2[N:20]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][CH:28]=[CH:27]4)[N:21]=[N:22][C:17]2=[N:16][CH:15]=1.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O>ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:14]1[N:19]=[C:18]2[N:20]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][CH:28]=[CH:27]4)[N:21]=[N:22][C:17]2=[N:16][CH:15]=1

参与物

7

反应物 4

HCID 8071乙二醇二甲醚HCID 10340Carbonic acid sodium salt (1:2)HCID 27343542-氟苯硼酸HCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

产物 1

HCID 593418296-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline收率 74.5%

试剂、催化剂与溶剂 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)催化剂HCID 6344二氯甲烷溶剂2 次

反应条件

温度
80 °C

实验过程

A mixture of DME (3.0 mL) and 1 M aqueous Na2CO3 (0.88 mL) was degassed by bubbling in Argon for 10 minutes. The mixture was transferred via syringe to a vial containing 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.29 mmol), 2-fluorophenylboronic acid (45 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.2 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 3.5 hours. The crude reaction mixture was diluted with dichloromethane then washed with water. The dichloromethane was dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was purified by column chromatography using gradient elution with ethyl acetate and dichloromethane to afford 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (77 mg, 74%).

后处理

  1. customwas degassed
  2. customby bubbling in Argon for 10 minutes
  3. customThe mixture was transferred via syringe
  4. customThe vial was capped
  5. customThe crude reaction mixture
  6. washthen washed with water
  7. dry with materialThe dichloromethane was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customThe residue was purified by column chromatography
  11. washelution with ethyl acetate and dichloromethane

来源与证据

ORD记录
ord-809f753e12c145829877418314079bb0
来源数据集
uspto-grants-2010_06
专利号
US07732604B2

关联笔记

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