反应详情

To a solution of 2-phenyl-2H-indazol-3-amine (300 mg, 1.4 mmol; Shirtcliff, Laura D.; Rivers, Jazmin; Haley, Michael M, Journal of Organic Chemistry (2006), 71(17), 6619-6622) in CH2Cl2 (16 ml) was added benzaldehyde (730 μl, 7.2 mmol; [100-52-7]), acetic acid (220 ul, 4.3 mmol) and sodium triacetoxyborohydride (912 mg, 4.3 mmol) at ambient temperature under an argon atmosphere. The reaction mixture was heated under reflux conditions for 64 h, poured onto ice water/aqueous NaHCO3 solution 1/1 and extracted two times with CH2Cl2. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure, the resulting yellow oil was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (470 mg, 1.5 mmol; quant.) as yellow solid. MS: m/e=298.1 [M+H+].

1. temperatureThe reaction mixture was heated under reflux conditions for 64 h
2. additionpoured onto ice water/aqueous NaHCO3 solution 1/1
3. extractionextracted two times with CH2Cl2
4. washThe combined extracts were washed with ice water/brine 1/1
5. dry with materialdried over Na2SO4
6. filtrationAfter filtration the solvent
7. customwas removed under reduced pressure
8. customthe resulting yellow oil was purified by column chromatography (silica gel, iPrOAc/heptane)