Tetrahydrofuran → HCID 90118173, Verbindung

HRID 523163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523163
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:3]=1.CN1CC(=O)OB([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)OC(=O)C1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1COCC1>CCOC(C)=O.[Cl-].[Na+].O.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].O>[Cl:1][C:2]1[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:5]=[C:4]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:3]=1

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 136008936-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dioneHCID 901181032-(4,6-Dichloropyridin-2-yl)thiazole

Produkt 1

HCID 90118173HCID 90118173, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a 2 dram vial equipped with a stir bar was added 2-(4,6-dichloropyridin-2-yl)thiazole (50 mg, 0.22 mmol), 6-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione (“phenylboronic acid MIDA ester”, 50 mg, 0.22 mmol), Pd(dppf)Cl2 (8 mg, 11 μmol) and K3PO4 (344 mg, 1.62 mmol). The vial was capped with a septum screwcap and then placed under N2 atmosphere. To the vial was added THF (1 mL) and water (0.5 mL). The mixture was placed in a 60° C. oil bath with stirring for 16 h. The reaction mixture was diluted with EtOAc (5 mL) and brine (1 mL). The mixture was shaken; the aq. phase was decanted away via pipet. The organic phase was dried over MgSO4; filtered; and the filtrate was concentrated in vacuo to afford a dark amber solid. This material was subjected to silica gel chromatography to afford 2-(4-chloro-6-phenylpyridin-2-yl)thiazole as a yellow solid (38 mg, 64%). 1H-NMR (400 MHz, CDCl3) δ 8.16 (d, J=1.8 Hz, 1H), 8.14-8.08 (m, 2H), 7.97 (d, J=3.0 Hz, 1H), 7.77 (d, J=1.8 Hz, 1H), 7.58-7.45 (m, 4H).

Aufarbeitung

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was capped with a septum screwcap
  3. customwas placed in a 60° C.
  4. stirringThe mixture was shaken
  5. customthe aq. phase was decanted away via pipet
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationand the filtrate was concentrated in vacuo
  9. customto afford a dark amber solid

Quellen und Nachweise

ORD-Eintrag
ord-021d27ea4d3c460d87c69304b9520f9f
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334279B2

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