Toluene → Methyl 2-(4-(pyridin-2-yl)phenyl)acetate

反応式

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C([N:16]([CH:19]([CH3:21])C)[CH2:17][CH3:18])(C)C.[C:22]1(C)C=CC=CC=1>>[N:16]1[CH:17]=[CH:18][CH:22]=[CH:21][C:19]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

参加物

反応物 3

HCID 1140Toluene

HCID 81531Diisopropylethylamine

HCID 316783Methyl 2-(4-bromophenyl)acetate

生成物 1

HCID 12094242Methyl 2-(4-(pyridin-2-yl)phenyl)acetate

実験手順

Under argon, 7.85 g (34.3 mmol) of methyl 4-bromophenylacetate are initially charged in 95 ml of toluene and, at room temperature, admixed with 7.97 g (61.7 mmol) of diisopropylethylamine, 9.50 g (37.7 mmol) of 2-trimethyl-stannylpyridine and 0.4 g (0.3 mmol) of tetrakis(triphenylphosphane)palladium(0). The mixture is then heated under reflux for 18 h. After cooling, the mixture is washed with in each case 100 ml of 1N hydrochloric acid and saturated sodium bicarbonate solution. The organic phase is discarded. The acidic and the basic aqueous phase are neutralized and in each case extracted with 100 ml of dichloromethane, and the combined organic phases are dried over sodium sulphate and freed from the solvent under reduced pressure. Example VII is obtained after silica gel chromatography (toluene/ethyl acetate gradient 5:1-1:1) as a colourless oil.