Methyl Acrylate → Ethyl (2E)-3-(5-formyl-2-pyridinyl)-2-propenoate

HRID 43356

반응식

HRID 43356 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].[C:16]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(=O)C.[Na+]>CN(C=O)C.[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]>[CH:8]([C:5]1[CH:6]=[CH:7][C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])=[N:3][CH:4]=1)=[O:9]

참가 물질

7

반응물 4

HCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 517045Sodium AcetateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

생성물 1

HCID 86628160Ethyl (2E)-3-(5-formyl-2-pyridinyl)-2-propenoate수율 93.7%

시약·촉매·용매 2

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-촉매HCID 6228Dimethylformamide용매

반응 조건

온도
170 °C

실험 절차

A mixture of 2-bromo-5-formylpyridine (500 mg, 2.6 mmol), methyl acrylate (0.6 ml, 6.5 mmol), tri-(o-tolyl)phosphine (80 mg, 0.26 mmol), allyl palladium (II) chloride dimer (47 mg, 0.13 mmol) and sodium acetate (1.08 g, 8 mmol) in DMF (10 ml) was heated at 170° C. in a microwave reactor for 0.75 h. The reaction mixture was filtered through Celite® then diluted with DCM and water. The organic phase was dried, concentrated in vacuo and purified by chromatography to give the title compound as a white solid (50 mg). δH (CDCl3, 250 MHz) 10.14 (1H, s), 9.09 (1H, d), 8.19 (1H, dd), 7.72 (1H, d), 7.57 (1H, d), 7.08 (1H, d), 3.85 (3H, s). MS (ES): MH+ 192.

후처리

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additionthen diluted with DCM and water
  3. customThe organic phase was dried
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography

출처 및 근거

ORD 기록
ord-c0809180160c4ca9954d8ce9512a8b6f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536182B2

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