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

HRID 574591

反応式

HRID 574591 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4039ab3e1293430cb8a2a4d8eb56f3f4
出典データセット
uspto-grants-2015_05
特許番号
US09034880B2

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