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

HRID 1987144
Notes
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Reaction equation

HRID 1987144 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d7990cb56eb24877a980a0b07f289575
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07550478B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes