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

HRID 540457Notizen

Reaktionsgleichung

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

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

customThe flask was sealed
temperatureThe reaction was cooled to room temperature
washwashed with water
filtrationfiltered
concentrationconcentrated
customThe resultant residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-99781a1120ca4bc7aa0d84ed422828ec
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08871738B2

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