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Potassium vinyltrifluoroborate → (5-Chloro-2-vinylpyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone

HRID 1987144
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HRID 1987144 반응식
Cl[C:2]1[C:7]([C:8]([C:10]2[C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=[C:12]([O:18][CH3:19])[C:11]=2[F:20])=[O:9])=[CH:6][C:5]([Cl:21])=[CH:4][N:3]=1.[CH:22]([B-](F)(F)F)=[CH2:23].[K+]>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:21][C:5]1[CH:6]=[C:7]([C:8]([C:10]2[C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=[C:12]([O:18][CH3:19])[C:11]=2[F:20])=[O:9])[C:2]([CH:22]=[CH2:23])=[N:3][CH:4]=1
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참가 물질

5

반응물 2

HCID 23679353Potassium vinyltrifluoroborateHCID 86609786(2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone

생성물 1

HCID 57722878(5-Chloro-2-vinylpyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 1031
1-Propanol
용매

실험 절차

To a stirred solution of (2,5-dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone (11.6 g, 35.6 mmol) in nPrOH (200 mL) were added potassium vinyltrifluoroborate (5.00 g, 37.3 mmol), PdCl2(dppf) (580 mg, 0.71 mmol), and TEA (4.96 mL, 35.6 mmol). The reaction mixture was purged with N2 for 10 min, heated to reflux for 3 h, cooled to room temperature, treated with water, and concentrated. The residue was extracted with EtOAc (×3). The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.63 (d, 1H); 7.62 (d, 1H); 7.41 (d, 1H); 7.36 (dd, 1H); 7.09 (t, 1H); 6.57 (dd, 1H); 6.54 (d, 1H); 5.63 (m, 2H); 5.23 (d, 1H); 3.92 (s, 3H). LRMS (ESI) calc'd for (C17H13ClFNO2) [M+H]+, 318.1; found 318.1.

후처리

  1. customThe reaction mixture was purged with N2 for 10 min
  2. temperatureheated
  3. temperatureto reflux for 3 h
  4. additiontreated with water
  5. concentrationconcentrated
  6. extractionThe residue was extracted with EtOAc (×3)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-d7990cb56eb24877a980a0b07f289575
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07550478B2

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