2-甲基-5-乙烯基吡啶 → 9-(2-(2-Methyl-5-pyridyl)ethyl)-6-bromo-3-methyl-1,2,3,4-tetrahydro-gamma-carboline

HRID 574591笔记

反应方程式

HRID 574591 反应方程式
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]=[CH2:24])=[CH:19][N:18]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:24][CH2:23][C:20]3[CH:19]=[N:18][C:17]([CH3:16])=[CH:22][CH:21]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

参与物

5

反应物 2

HCID 88172-甲基-5-乙烯基吡啶HCID 1998168-溴-1-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-B]吲哚

产物 1

HCID 6164959-(2-(2-Methyl-5-pyridyl)ethyl)-6-bromo-3-methyl-1,2,3,4-tetrahydro-gamma-carboline收率 8.7%

试剂、催化剂与溶剂 2

HCID 70681四丁基氯化铵催化剂HCID 14798氢氧化钠溶剂

实验过程

Tetra butyl ammonium chloride (0.026 g, 0.094 mmol) was taken in 15 ml, 50% aq. NaOH solution (7 ml) and stirred for 15 minutes at RT. 8-bromo-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.500 gm, 1.89 mmole) was added and further stirred for 10 min. at RT. 2-methyl-5-vinylpyridine (0.247 gm, 2.08 mmole) was added and reaction mixture was heated at 100° C. for 12-15 hrs. The reaction mixture was cooled at RT, extracted with ethyl acetate, dried over anhydrous sodium sulphate, concentrated and purified by Reverse Phase HPLC to get 63 mg 8-bromo-2-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as TFA Salt.

后处理

  1. stirringfurther stirred for 10 min. at RT
  2. customreaction mixture
  3. temperaturewas heated at 100° C. for 12-15 hrs
  4. temperatureThe reaction mixture was cooled at RT
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. custompurified by Reverse Phase HPLC

来源与证据

ORD记录
ord-4039ab3e1293430cb8a2a4d8eb56f3f4
来源数据集
uspto-grants-2015_05
专利号
US09034880B2

反应笔记

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