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

HRID 710910

Reaction equation

HRID 710910 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2c54075615e24a3c88d99f9b2e2b77b6
Source dataset
uspto-grants-2015_11
Patent number
US09181240B2

Linked notes

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