O-Xylene → 4-Cyclopropyl-3-nitropyridine

Temperatur

130 °C

4-Chloro-3-nitropyridine (100 mg, 0.630 mmol) and cyclopropyl boronic acid (10.0 mg, 0.091 mmol) were added to a solution of xylene (3 mL) previously purged with argon (10 min). The reaction mixture was purged with argon for a further 15 mins, followed by the addition of potassium carbonate (174.35 mg, 1.26 mmol) and Pd(PPh3)4 (34.5 mg, 0.063 mmol). The resulting mixture was heated to reflux at 130° C. overnight. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was cooled and concentrated to afford the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 110 mg of the product (100% yield). LCMS: 99.09%, m/z=165 (M+1)

1. custompreviously purged with argon (10 min)
2. customThe reaction mixture was purged with argon for a further 15 mins
3. temperatureThe resulting mixture was heated
4. temperatureThe reaction mixture was cooled
5. concentrationconcentrated
6. customto afford the crude product
7. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

ORD-Eintrag

ord-30041b14b6114ed2b7384ac79b9e3e78

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08946260B2