2-Methyl-5-vinylpyridine → 1H-Pyrido(4,3-b)indole, 2,3,4,5-tetrahydro-2-ethyl-8-methyl-5-(2-(6-methyl-3-pyridyl)ethyl)-

HRID 574365Notes

Reaction equation

HRID 574365 reaction equation
[CH2:1]([N:3]1[CH2:16][CH2:15][C:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2].[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][N:19]=1.[H-].[Na+]>CS(C)=O>[CH2:1]([N:3]1[CH2:16][CH2:15][C:6]2[N:7]([CH2:25][CH2:24][C:21]3[CH:20]=[N:19][C:18]([CH3:17])=[CH:23][CH:22]=3)[C:8]3[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 88172-Methyl-5-vinylpyridineHCID 24758Sodium hydrideHCID 594550662-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 2129291H-Pyrido(4,3-b)indole, 2,3,4,5-tetrahydro-2-ethyl-8-methyl-5-(2-(6-methyl-3-pyridyl)ethyl)-Yield 3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Preparation of the title compound was carried out according to General Method 2. 2-Ethyl-2,3,4,5-tetrahydro-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-1H-pyrido[4,3-b]indole was prepared from 2-ethyl-2,3,4,5-tetrahydro-8-methyl-1H-pyrido[4,3-b]indole (See Example 6) (214 mg, 1 mmol), 2-methyl-5-vinylpyridine (1 mL, 2.3 mmol) and NaH (120 mg, 3 mmol) in DMSO (4 ml) at 120° C. for 48 h to obtain 10 mg of 2-ethyl-2,3,4,5-tetrahydro-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-1H-pyrido[4,3-b]indole after purification.

Sources & evidence

ORD record
ord-de59b049387c4331a9999a919324f55f
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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