Hydrazine → 6-Methyl-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

In a microwave vial 2-chloro-6-methylpyridine-3-carbaldehyde (1.98 g, 12.7 mmol) was dissolved in 1,4-dioxane (12 mL) and hydrazine (6.0 mL, 191 mmol) was added. The vial was sealed and heated under microwave irradiation at 150° C. for 1 h. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with brine then dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 50% to 100% EtOAc/heptane to provide 863 mg (41%) of 6-methyl-1H-pyrazolo[3,4-b]pyridine as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.06 (s, 1H), 8.03 (d, J=8.3 Hz, 1H), 7.07 (d, J=8.3 Hz, 1H), 2.79 (s, 3H).

Provenance & Evidence