5-Bromo-2-methoxypyridine → 5-(3,4-Dimethoxyphenyl)-2-methoxypyridine

HRID 1654671

Reaktionsgleichung

C[Sn](C)(C)[C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][N:18]=1>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[N:18][CH:19]=2)[CH:8]=[CH:7][C:6]=1[O:9][CH3:10]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A solution of 2.00 g (6.64 mmol) of 4-trimethylstannylveratrole, 2.49 g (13.2 mmol) of 2-methoxy-5-bromopyridine and 370 mg (0.332 mmol) of Pd (PPh3)4 in 30 mL of dry dimethylformamide is flushed thoroughly with nitrogen and heated to 90° C. for 12 hours. The reaction mixture is partitioned between ethyl acetate (150 mL) and water (100 mL). The aqueous layer is back extracted with ethyl acetate (100 mL) and the combined organics are washed with brine (75 mL), dried (MgSO4) and evaporated to give a crude yellow oil. The oil is chromatographed on silica gel (eluting with 95:5 hexane/ethyl acetate and then with 9:1 hexane/ethyl acetate) which gives 5-(3,4-dimethoxyphenyl)-2-methoxypyridine (m.p 83°-84° C.)

Aufarbeitung

customThe reaction mixture is partitioned between ethyl acetate (150 mL) and water (100 mL)
extractionThe aqueous layer is back extracted with ethyl acetate (100 mL)
washthe combined organics are washed with brine (75 mL)
dry with materialdried (MgSO4)
customevaporated
customto give a crude yellow oil
customThe oil is chromatographed on silica gel (
washeluting with 95:5 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-6834719e306844f8a3e1a01da76bb1c4
Quelldatensatz: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05409930

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