Ethyl bromoacetate → Ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate

HRID 517836Notes

Reaction equation

HRID 517836 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)CC)C.Cl.[CH3:26][N:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1>C(O)C>[CH3:26][N:27]1[CH2:32][CH2:31][C:30]2[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:29]=2[CH2:28]1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 44158421Ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according by using p-tolylhydrazine hydrochloride, ethyl bromoacetate, triethylamine and N-methyl-4-piperidone hydrochloride in ethanol to obtain ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate after purification on neutral alumina chromatography eluting with dichloromethane-hexane gradient.

Sources & evidence

ORD record
ord-0ef60443a43f46a3a9b27b4530f58403
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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