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

HRID 509670Notes

Reaction equation

HRID 509670 reaction equation
[CH2:1]([N:3]1[CH2:15][CH2:14][C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2].C([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=C.[Na].FC(F)(F)C([O-])=O>C(O)C.[O-]S([O-])(=O)=O.[Cu+2]>[CH2:1]([N:3]1[CH2:15][CH2:14][C:6]2[N:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 75212-VinylpyridineHCID 84468TrifluoroacetateHCID 5888242-Ethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleHCID 5360545Sodium

Product 1

HCID 687557142-ethyl-2,3,4,5-tetrahydro-5-(2-pyridyl)-1H-pyrido[4,3-b]indoleYield 2.9%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared according to General Method 3. 2-Ethyl-2,3,4,5-tetrahydro-5-(2-pyridyl)-1H-pyrido[4,3-b]indole was prepared from 2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (See Example 5) (200 mg, 1 mmol), 2-vinylpyridine (0.26 mg, 2.5 mmol), sodium (15 mg, 0.65 g atom) and CuSO4 (10 mg, catalytic) in ethanol (2 mL) at 150° C. for 16 h to obtain 8 mg of 2-ethyl-2,3,4,5-tetrahydro-5-(2-pyridyl)-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-9f4cf6e04aa4421fbd4a7cf8636c206e
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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