3-Methyl-2-(tributylstannyl)pyridine → Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate

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Reaktionsgleichung

Br[C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH3:13][C:14]1[C:15]([Sn](CCCC)(CCCC)CCCC)=[N:16][CH:17]=[CH:18][CH:19]=1>C1(C)C=CC=CC=1.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>[CH3:13][C:14]1[C:15]([C:2]2[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=2)=[N:16][CH:17]=[CH:18][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To the title compound of step B (509 mg, 2.2 mmol) and the title compound of step C (1.1 g, 2.9 mmol) in PhCH3 (6.6 mL) was added Pd(PPh3)4 (225 mg, 0.2 mmol). The reaction was degassed with N2 and heated at 150° C. for 1.5 h using microwave reactor. The reaction was cooled to rt, diluted with H2O and extracted with EtOAc. The organic layer was dried (MgSO4). Purification via silica gel chromatography (0-100% EtOAc in heptane) gave the title compound (101 mg, 18%). MS (ESI) mass calcd. for C14H14N2O2, 242.3; m/z found 243 [M+H]+.

Aufarbeitung

customThe reaction was degassed with N2
temperatureThe reaction was cooled to rt
additiondiluted with H2O
extractionextracted with EtOAc
dry with materialThe organic layer was dried (MgSO4)
customPurification via silica gel chromatography (0-100% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag: ord-8354ce1514984632a8d94ed947c04494
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09062078B2

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