2,3-Diaminotoluene → HCID 178424027, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde Compound 5a (50 mg, 0.22 mmol) and 3-methyl-benzene-1,2-diamine Compound 5b (27 mg, 0.22 mmol) and sulfur (9 mg, 0.28 mmol) in DMF (1 mL) was heated to 100° C. overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-3-(4-methyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridine Compound 5c (50 mg, 69% yield) as a grey powder. 1H NMR (400 MHz, MeOD) δ 9.03 (s, 1H), 8.68 (s, 1H), 7.18 (t, 1H, J=8.4 Hz), 7.09 (m, 2H), 2.69 (s, 3H); MS (ESI) m/z: 329 (M+H+).

Provenance & Evidence