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

HRID 517821Notes

Reaction equation

HRID 517821 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=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>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][C:29]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 44159218Ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetateYield 15.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 1 by using 4-chlorophenylhydrazine hydrochloride (5 g, 27.9 mmol), ethyl bromoacetate (4.6 g, 27.9 mmol), triethylamine (11.6 mL, 83.2 mmol) and N-methyl-4-piperidone hydrochloride (5.2 g, 34.9 mmol) in ethanol (50 ml) to obtain 1.3 g of ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate after purification on neutral alumina chromatography eluting with dichloromethane-hexane gradient.

Sources & evidence

ORD record
ord-ab56054eeecb41dd9ae1bbb7a7e3a7a6
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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