4-Aminopyridine → Methyl 2-(pyridin-4-ylamino)benzoxazole-4-carboxylate

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Reaktionsgleichung

Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C([O-])([O-])=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(O)(C)C>[N:19]1[CH:20]=[CH:21][C:16]([NH:15][C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)=[CH:17][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (350 mg, 1.65 mmol), 4-aminopyridine (233 mg, 2.48 mmol), palladium(II) acetate (7.4 mg, 0.033 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (39 mg, 0.083 mmol), K2CO3 (570 mg, 4.13 mmol) and t-BuOH (4 mL) was heated to 90° C. for 40 min. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth and concentrated. The crude product was purified by column chromatography (silica gel, 9:1 CH2Cl2/CH3OH) to afford methyl 2-(pyridin-4-ylamino)benzoxazole-4-carboxylate. 1H NMR and MS consistent.

Aufarbeitung

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered through diatomaceous earth
concentrationconcentrated
customThe crude product was purified by column chromatography (silica gel, 9:1 CH2Cl2/CH3OH)

Quellen und Nachweise

ORD-Eintrag: ord-64aad37a3af54c31889d64be9c5b2f5a
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07863271B2

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