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

HRID 1987144
ノート
印刷プレビュー

反応式

HRID 1987144 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d7990cb56eb24877a980a0b07f289575
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07550478B2

反応ノート

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