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

HRID 2213528Notes

Reaction equation

HRID 2213528 reaction equation
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

Participants

4

Reactant 3

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

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

Procedure

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.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 18 h
  3. temperatureAfter cooling
  4. washthe mixture is washed with in each case 100 ml of 1N hydrochloric acid and saturated sodium bicarbonate solution
  5. extractionextracted with 100 ml of dichloromethane
  6. dry with materialthe combined organic phases are dried over sodium sulphate
  7. customExample VII is obtained after silica gel chromatography (toluene/ethyl acetate gradient 5:1-1:1) as a colourless oil

Sources & evidence

ORD record
ord-c3e382950c7c43939931d5780fa12487
Source dataset
uspto-grants-2006_09
Patent number
US07105553B2

Reaction notes

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