Imidazole → 5-(tert-butyldimethylsilanyloxymethyl)-3-iodo-1-methyl-1H-indazole

Participants

Reaction Steps

To a solution of (3-iodo-1-methyl-1H-indazol-5-yl)-methanol (810 mg, 2.81 mmol) in DMF (9 mL) was added imidazole (479 mg, 7.03 mmol) followed by tert-butyldimethylsilyl chloride (466 mg, 3.09 mmol). The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with EtOAc (2×). The combined organics were washed with water (3×) then dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 10% EtOAc/hexanes to afford 732 mg (65%) of 5-(tert-butyldimethylsilanyloxymethyl)-3-iodo-1-methyl-1H-indazole as a pale yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.26-7.34 (m, 2H), 7.17-7.23 (m, 1H), 4.73 (s, 2H), 3.97 (s, 3H), 0.84 (s, 9H), 0.00 (s, 6H).

Provenance & Evidence