1H-Indazole → HCID 67282655, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 1H-indazole (0.47 g, 4.0 mmol), (3-iodophenyl)methanol (1.4 g, 6.0 mmol), ferric chloride (0.13 g, 0.8 mmol), and tri-potassium phosphate monohydrate (1.84 g, 8.0 mmol). Degassed water (2 mL) was then added followed by (1R,2R)—N,N′-dimethylcyclohexane-1,2-diamine (0.25 mL, 1.6 mmol). The reaction mixture was then heated to 135° C. and stirred overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford [3-(1H-indazol-1-yl)phenyl]methanol (0.67 g, 74%). LC-MS: (FA) ES+ 225.

Provenance & Evidence