Tert-Butylamine → N-tert-butyl-4-(difluoromethyl)pyridin-2-amine

Temperatur

100 °C

A suspension of 4-difluoromethyl-pyridine-N-oxide (4.95 g, 34.1 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (20.7 g, 44.3 mmol), triethylamine (15.6 mL, 111 mmol), and anhydrous tert-butylamine (4.6 mL, 43 mmol) in DCE (100 mL, 0.33 M) was sealed in pressure tube and stirred at 100° C. for 3.5 hr. After cooling to rt, the mixture was diluted with CH2Cl2 and washed with sat. aq. NaHCO3. The organics were dried over MgSO4 and following concentration, the reaction residue was purified by flash column chromatography (100:0-80:20 heptanes/EtOAc) to afford N-tert-butyl-4-(difluoromethyl)pyridin-2-amine as a yellow liquid (4.43 g, 65%); 1H NMR (400 MHz, CDCl3) δ 8.15 (d, J=5.2 Hz, 1H), 6.65-6.28 (m, 3H), 4.62 (br s, 1H), 1.44 (s, 9H).

1. customwas sealed in pressure tube
2. temperatureAfter cooling to rt
3. washwashed with sat. aq. NaHCO3
4. dry with materialThe organics were dried over MgSO4
5. concentrationconcentration
6. customthe reaction residue was purified by flash column chromatography (100:0-80:20 heptanes/EtOAc)

ORD-Eintrag

ord-a2a0f222d2ad4652b9f30c5e94e21303

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09399636B2