Stannous chloride dihydrate → 6-(4-chloro-1H-imidazol-1-yl)pyridin-3-amine

Temperature

90 °C

A vial was charged with 2-(4-chloro-1H-imidazol-1-yl)-5-nitropyridine (675 mg, 3.01 mmol), tin(II) chloride dihydrate (2.03 g, 9.02 mmol), and methanol (10 mL). The vial was sealed and heated to 90° C. and stirred for 16 hours. The reaction was cooled to room temperature and concentrated. The residue was taken up in water (20 mL) and neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate (3×50 mL) and the combined organics were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave 6-(4-chloro-1H-imidazol-1-yl)pyridin-3-amine (380 mg, 65%) as a light yellow solid. 1H NMR (400 MHz, CD3OD, δ): 8.20 (d, J=1.6 Hz, 1H), 7.89 (d, J=2.4 Hz, 1H), 7.68 (d, J=1.6 Hz, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.21 (dd, J=8.8, 2.8 Hz, 1H).

1. customThe vial was sealed
2. temperatureThe reaction was cooled to room temperature
3. concentrationconcentrated
4. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
5. dry with materialthe combined organics were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash column chromatography

ORD record

ord-fc5eaceef4024797867ac2d6f8d80b99

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073871B2