1,4-Dioxane → Tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate

HRID 529716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529716
Br[C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1B1OC(C)(C)C(C)(C)O1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O1CCOCC1>C(OCC)(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.[Pd+2].O>[Cl:10][C:4]1[CH:3]=[C:2]([C:32]2[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:21][C:20]=2[CH3:19])[CH:7]=[N:6][C:5]=1[O:8][CH3:9]

Komponenten

9

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 404270045-Bromo-3-chloro-2-methoxypyridineHCID 68937270Tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Produkt 1

HCID 86682280Tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoateAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 17952575palladium(II)dichloromethaneKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a 250 mL RBF was added 5-bromo-3-chloro-2-methoxypyridine (1.5 g), tribasic potassium phosphate (2.86 g, 13.5 mmol), bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.275 g, 6.74 mmol), tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.27 g, 7.13 mmol), dioxane (50 mL) and water (3 mL). The flask was sealed and was stirred at 80° C. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water, filtered and concentrated. The resultant residue was purified by column chromatography to yield tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate (2.0 g, 5.99 mmol). MS ESI calc'd. for C18H21ClNO3 [M+H]+ 334.1, found 334.0.

Aufarbeitung

  1. customThe flask was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15506110a8904d8d95aeca17b1be198c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346825B2

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