2-Vinylpyridine → 2-methyl-5-(2-(pyridin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 509671Notes

Reaction equation

HRID 509671 reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[CH2:16].[Na].FC(F)(F)C([O-])=O>C(O)C.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[N:6]([CH2:16][CH2:15][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

7

Reactant 4

HCID 75212-VinylpyridineHCID 84468TrifluoroacetateHCID 974242-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleHCID 5360545Sodium

Product 1

HCID 545868122-methyl-5-(2-(pyridin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 20.6%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared according to General Method 3. 2,3,4,5-Tetrahydro-2-methyl-5-(2-(pyridin-2-yl)ethyl)-1H-pyrido[4,3-b]indole was prepared from 2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (See Example 3) (200 mg, 1 mmol), 2-vinylpyridine (0.26 mg, 2.5 mmol), sodium (5 mg, 0.21 g atom) and CuSO4 (5 mg, catalytic) in ethanol (4 mL) at 120° C. for 16 h (overnight) to obtain 60 mg of 2,3,4,5-tetrahydro-2-methyl-5-(2-(pyridin-2-yl)ethyl)-1H-pyrido[4,3-b]indole as a trifluoroacetate salt after purification on reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-71cd941f6a664d109acd348bc66a1d3c
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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