Ethyl Acrylate → ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate

HRID 226357

반응식

HRID 226357 반응식
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C.[C:41]([O:45][CH2:46][CH3:47])(=[O:44])[CH:42]=[CH2:43]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:1][C:2]1[N:3]=[CH:4][C:5](/[CH:43]=[CH:42]/[C:41]([O:45][CH2:46][CH3:47])=[O:44])=[CH:6][C:7]=1[CH3:8]

참가 물질

8

반응물 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 101086802-Bromo-5-iodo-3-methylpyridine

생성물 1

HCID 86603663ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2-bromo-5-iodo-3-methylpyridine (1.5 g) in DMF (15 mL) was added palladium(II) acetate (56.5 mg) and tri-o-tolylphosphine (230 mg) and diisopropylethylamine (3.5 mL), and ethyl acrylate (1.09 mL). The mixture was heated at 90° C. for 1 hour. Resulting mixture was poured into water and extracted with AcOEt. The organic layer was washed with water and brine, and dried over Na2SO4, and the solvent was removed in vacuo. Residual brown oil was purified by silica gel column chromatography eluted with AcOEt and hexane (1:4-1:2) to give ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate (1.00 g) as pale yellow powder.

후처리

  1. customResulting mixture
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customwas purified by silica gel column chromatography
  7. washeluted with AcOEt and hexane (1:4-1:2)

출처 및 근거

ORD 기록
ord-1526812b5b584f43bb9038b3b0fb20ce
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

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