反应详情

温度

0 °C

An oven-dried flask under N2 (g) was charged with NaH (60% wt) (592 mg, 14.8 mmol) and THF (30 mL) and the suspension cooled to 0° C. CH3PPh3Br (5.29 g, 14.8 mmol) was added and stirred for 30 min at which time 1-(4-methoxybenzyl)-1H-indazole-6-carbaldehyde (1.97 g, 7.40 mmol) was added and the reaction was allowed to slowly warm to room temperature. After 2.5 h quenched with NH4Cl and extracted with Et2O. The organic layers were washed with brine (2×) and dried over MgSO4. The solvent was removed and the residue purified using Biotage Isolera (silica gel, 10-20% EtOAc in hexane) to give the title compound as a white solid (1.20 g, 61%); 1H NMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 7.67 (d, J=8.8 Hz, 1H), 7.30-7.26 (m, 2H), 7.16 (d, J=8.3 Hz, 2H), 6.84-6.76 (m, 3H), 5.80 (d, J=17.5 Hz, 1H), 5.53 (s, 2H), 5.30 (d, J=10.9 Hz, 1H), 3.76 (s, 3H); MS ESI 264.9 [M+H]+, calcd for [C17H16N2O+H]+ 265.1.

1. additionwas added
2. temperatureto slowly warm to room temperature
3. customAfter 2.5 h quenched with NH4Cl
4. extractionextracted with Et2O
5. washThe organic layers were washed with brine (2×)
6. dry with materialdried over MgSO4
7. customThe solvent was removed
8. customthe residue purified