反应详情

温度

0 °C

To a suspension of 3-iodo-1H-indazole-6-carbaldehyde (126.6 mg, 0.46 mmol) in CH2Cl2 (5 mL) and 50% aq. KOH (1.0 mL) was added tetrabutylammonium bromide (3.4 mg, 0.01 mmol) and the solution cooled to 0° C. (2-(Chloromethoxy)ethyl)trimethylsilane (0.10 mL, 0.56 mmol) was then added dropwise and the reaction stirred at 0° C. for 1.5 hours. The solution was then transferred to a sep. funnel containing ethyl acetate (200 mL) and the organic layer was washed with water (2×20 mL) and brine (20 mL), dried (Na2SO4) and the solvent removed in vacuo. The resulting residue was adsorbed onto silica using dichloromethane-methanol to dissolve, and evaporated to dryness. Chromatography (10 g silica SPE tube, Silicycle, 50-100% dichloromethane in hexane, 10% ethyl acetate in dichloromethane) to give 88 mg, 47%. 1H NMR: (400 MHz, CDCl3) δ 10.12 (s, 1H), 8.05 (m, 2H), 7.67 (d, J=9.2 Hz, 1H), 5.77 (s, 2H), 3.60 (m, 2H), 0.90 (m, 2H), −0.048 (s, 9H).

1. additionwas then added dropwise
2. washthe organic layer was washed with water (2×20 mL) and brine (20 mL)
3. dry with materialdried (Na2SO4)
4. customthe solvent removed in vacuo
5. dissolutionto dissolve
6. customevaporated to dryness
7. customChromatography (10 g silica SPE tube, Silicycle, 50-100% dichloromethane in hexane, 10% ethyl acetate in dichloromethane) to give 88 mg, 47%