Triphenylphosphine → 6-bromo-4-methylene-3,4-dihydro-2H-pyrano[3,2-b]pyridine

HRID 1478547

반응식

HRID 1478547 반응식
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+].Br[C:26]1[C:31]([O:32][CH2:33][CH2:34][CH:35]=[CH2:36])=[CH:30][CH:29]=[C:28]([Br:37])[N:27]=1>[N+](CC)(CC)(CC)CC.[Cl-].CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:37][C:28]1[N:27]=[C:26]2[C:35](=[CH2:36])[CH2:34][CH2:33][O:32][C:31]2=[CH:30][CH:29]=1

참가 물질

8

반응물 3

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 584840892,6-Dibromo-3-(but-3-enyloxy)pyridine

생성물 1

HCID 584840716-bromo-4-methylene-3,4-dihydro-2H-pyrano[3,2-b]pyridine

시약·촉매·용매 4

HCID 5946Tetraethylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
105 °C

실험 절차

To a stirred mixture of PPh3(67.6 g, 0.258 mol), KOAc (42 g, 0.43 mol), Pd(OAc)2 (1.94 g, 8.6 mmol) and Et4NCl (28.6 g, 0.172 mmol), was added 2,6-dibromo-3-(but-3-enyloxy) pyridine (26.4 g, 0.086 mol) in anhydrous DMF (300 ml). The mixture was heated at 105° C. overnight. After cooling to rt, the mixture was dissolved in EtOAc, washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography (petroleum) to afford the title compound as an oil.

후처리

  1. temperatureAfter cooling to rt
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography (petroleum)

출처 및 근거

ORD 기록
ord-74758aa85cad44d1b52f3869b620be18
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403845B2

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