2-Bromopyridine → (+/-)-Ethyl 4-(pyridin-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate

Temperatur

100 °C

In a sealable tube, tris(dibenzylideneacetone) dipalladium (0) (5.2 mg, 0.0056 mmol), (S)-BINAP (10.7 mg, 0.017 mmol), cesium carbonate (132 mg, 0.41 mmol), 2-bromopyridine (33 □L, 0.35 mmol), and ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (Example 3a, 60 mg, 0.29 mmol) were dissolved in dioxane (2 mL). The reaction vessel was sealed and the suspension was heated at 100° C. for 20 h. The reaction mixture was cooled to ambient temperature, diluted with water (15 mL), and the product was extracted with dichloromethane (3×20 mL). The organic fractions were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (15% to 25% EtOAc/hexane) afforded the title compound (46 mg, 0.16 mmol). MS m/z: 285 (M+1).

1. customThe reaction vessel was sealed
2. temperatureThe reaction mixture was cooled to ambient temperature
3. extractionthe product was extracted with dichloromethane (3×20 mL)
4. dry with materialThe organic fractions were dried over sodium sulfate
5. concentrationconcentrated
6. customPurification of the product by flash column chromatography (15% to 25% EtOAc/hexane)

ORD-Eintrag

ord-51e9447c75b04d669f08eb89eb40d763

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07872009B2