Triethylamine → 2,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 574404Notes

Reaction equation

HRID 574404 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][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[N:18][CH:19]=1.C(N(CC)CC)C.O=[C:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:41])[Cl:40])=[O:36])[CH2:31][CH2:30]1>C(O)C>[CH3:10][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:12][CH2:13][C:14]3[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[C:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:40])[Cl:41])=[O:36])[CH2:31][C:30]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 152523022,2,2-Trichloroethyl 4-oxopiperidine-1-carboxylateHCID 533058565-(2-Bromoethyl)-2-methylpyridine

Product 1

HCID 578759452,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 10.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. p-Tolylhydrazine hydrochloride (5 g, 31.5 mmol), 5-(2-bromoethyl)-2-methylpyridine (6.3 g, 31.5 mmol), triethyl amine (13 ml, 94.5 mmol) and 2,2,2-trichloroethyl 4-oxopiperidine-1-carboxylate (563 mg, 2 mmol) were taken in ethanol (15 ml) to obtain 100 mg of 2,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-1H-pyrido[4,3-b]indole-2(5H)-carboxylate after purification on silica gel (230-400 mesh) chromatography eluting with acetone-hexane gradient.

Sources & evidence

ORD record
ord-59005064c8214eb88806e97e8bb6aaa8
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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