Potassium Carbonate → Diethyl-2-(2-methyl-6-quinolinyl)-2-butenedioate

HRID 1715195Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[C:13]([O:22][CH2:23][CH3:24])(=[O:21])/[CH:14]=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2)=[CH:14][C:13]([O:22][CH2:23][CH3:24])=[O:21])[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 6-bromo-2-methylquinoline (2.89 g) in DMF (70 mL) at room temperature, diethyl maleate (4.85 mL), palladium acetate (0.15 g), tri(o-tolyl)phosphine (0.39 g) and potassium carbonate (3.59 g) were subsequently added then the reaction mixture was warmed to 100° C. and stirring continued overnight. After cooling, the reaction mixture was quenched with water and extracted twice with diethyl ether. The combined organic layers were collected, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (eluting with cyclohexane-ethyl acetate from 100 to 60%) to give 4 g of the title compound as a slightly yellow oil.

Workup

temperatureAfter cooling
customthe reaction mixture was quenched with water
extractionextracted twice with diethyl ether
customThe combined organic layers were collected
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography on silica gel (eluting with cyclohexane-ethyl acetate from 100 to 60%)

Sources & evidence

ORD record: ord-bd0fd675f5d44109a7ffd8b79ba1275f
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799815B2

Reaction notes

Loading…