Potassium Phosphate, Tribasic → HCID 90117930, Verbindung

HRID 523148

Reaktionsgleichung

Reaktionsgleichung von HRID 523148
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=1.CN1CC(=O)OB([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)OC(=O)C1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=[C:2]([C:34]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 713108046-Methyl-2-(pyridin-3-yl)-1,3,6,2-dioxazaborocane-4,8-dioneHCID 901180792,4-Dichloro-6-(4-isopropoxyphenyl)pyridine

Produkt 1

HCID 90117930HCID 90117930, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Versuchsvorschrift

To a 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (60 mg, 0.21 mmol), 6-methyl-2-(3-pyridinyl)-1,3,6,2-dioxazaborocane-4,8-dione (“4-pyridyl MIDA boronate”, 50 mg, 0.21 mmol), Pd(dppf)Cl2 (8.0 mg, 10 μmol) and K3PO4 (337 mg, 1.59 mmol). The vial was capped with a septum screw-cap and then placed under N2 atmosphere. To the vial was added degassed THF (5 mL) and degassed water (1 mL). The vial was placed in a 60° C. heating block with stirring for 3 hours. The reaction mixture was cooled to room temperature and the aqueous phase was decanted. The organic solution was concentrated under a stream of N2 and the resulting solid residue was subjected to silica gel chromatography (hexanes:EtOAc) to afford 4-chloro-6-(4-isopropoxyphenyl)-2,4′-bipyridine as a white solid (45 mg, 65%). 1H-NMR (400 MHz, CDCl3) δ 8.84-8.81 (m, 2H), 8.16-8.11 (m, 2H), 8.00-7.97 (m, 3H), 7.04-6.99 (m, 2H), 4.69 (spt, J=6.0 Hz, 1H), 1.40 (d, J=6.0 Hz, 6H); MS: MS m/z 326.2 (M++1).

Aufarbeitung

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was capped with a septum
  3. customscrew-cap
  4. additionTo the vial was added
  5. customdegassed THF (5 mL)
  6. customdegassed water (1 mL)
  7. customwas placed in a 60° C.
  8. temperatureheating block
  9. customthe aqueous phase was decanted
  10. concentrationThe organic solution was concentrated under a stream of N2

Quellen und Nachweise

ORD-Eintrag
ord-7dcc9099975f4842acc8445524f4f94a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334279B2

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