Potassium Phosphate, Tribasic → HCID 90009177, Verbindung

HRID 531248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531248
COC1N=CC([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][C:10]=2[CH3:22])=CC=1B1OC(C)(C)C(C)(C)O1.Br[C:33]1[CH:34]=[C:35]([Cl:40])[C:36]([Cl:39])=[N:37][CH:38]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[Cl:40][C:35]1[CH:34]=[C:33]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[CH:11][C:10]=2[CH3:22])[CH:38]=[N:37][C:36]=1[Cl:39]

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 127477605-Bromo-2,3-dichloropyridineHCID 89522254HCID 89522254, Verbindung2×

Produkt 1

HCID 90009177HCID 90009177, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A suspension of tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (from INTERMEDIATE 31 Step B, 1.0 g, 3.14 mmol), 5-bromo-2,3-dichloropyridine (0.784 g, 3.46 mmol), potassium phosphate (1.33 g, 6.29 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.077 g, 0.094 mmol) in dioxane (12 mL) and water (1 mL) was flushed with nitrogen and stirred at 70° C. for 4 hours. After cooling down, the mixture was filtered over celite and the filter cake washed with ethyl acetate. The filtrate was diluted with ethyl acetate and water and partitioned. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated. The crude isolate was purified by silica gel chromatography (0 to 80% ethyl acetate/hexane) to give the titled compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.3 (d, J=2.1 Hz, 1H), 7.95 (s, 1H), 7.92 (d, J=7.7 Hz, 1H), 7.78 (d, J=2.0 Hz, 1H), 7.27 (d, J=7.9 Hz, 1H), 2.35 (s, 3H), 1.65 (s, 9H).

Aufarbeitung

  1. customwas flushed with nitrogen
  2. temperatureAfter cooling down
  3. filtrationthe mixture was filtered over celite
  4. washthe filter cake washed with ethyl acetate
  5. additionThe filtrate was diluted with ethyl acetate and water
  6. custompartitioned
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated
  11. customThe crude isolate
  12. customwas purified by silica gel chromatography (0 to 80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-77dbc3efedd84d509e2df75da047acd5
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353101B2

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