2-Methyl-5-vinylpyridine → 9-(2-(2-Methyl-5-pyridyl)ethyl)-6-bromo-3-methyl-1,2,3,4-tetrahydro-gamma-carboline

HRID 2196035

반응식

HRID 2196035 반응식
[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

참가 물질

5

반응물 2

HCID 88172-Methyl-5-vinylpyridineHCID 1998168-Bromo-2,3,4,5-tetrahydro-2-methyl-1H-pyrido(4,3-b)indole

생성물 1

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

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2d781a4069e34c11840d0ce130d4c505
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338408B2

연결된 노트

불러오는 중…