Ethanol → 5-Bromo-6-(cyclopropylmethoxy)-3-pyridinamine

Temperature

50 °C

A mixture of 3-bromo-2-(cyclopropylmethoxy)-5-nitropyridine (1 g, 3.7 mmol), ammonium chloride (600 mg, 11.1 mmol), and iron powder (1.05 g, 19 mmol) suspended in THF (6.2 mL), water (2.3 mL) and ethanol (6.2 mL) was heated to 100° C. using microwave irradiation (normal) for 5 h. The crude reaction mixture was filtered through a short plug of celite; the celite plug was washed with warm (50° C.) MeOH (50 mL). The resulting filtrate was concentrated in vacuo. The resulting residue was diluted with EtOAc (100 ml) and washed with saturated bicarbonate solution (aq), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound, (539 mg, 60%). LCMS (M+H)+=244.

1. custommicrowave irradiation (normal) for 5 h
2. customThe crude reaction mixture
3. filtrationwas filtered through a short plug of celite
4. washthe celite plug was washed
5. concentrationThe resulting filtrate was concentrated in vacuo
6. additionThe resulting residue was diluted with EtOAc (100 ml)
7. washwashed with saturated bicarbonate solution (aq)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-531ad0caf838480a886cd3445d5870e8

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115114B2