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 minutes). The reaction mixture was purged with argon for a further 15 minutes, 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% ethylacetate 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 Purity: 99%, m/z=165 (M+1)

1. custompreviously purged with argon (10 minutes)
2. customThe reaction mixture was purged with argon for a further 15 minutes
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-09fbe57d94aa4f698b6bb7f10e4c5711

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09029399B2