反応 #51280

反応方程式

Water

indazole amide

1-bromo-3-methoxypropane

NaH

→

3-methoxypropyl indazole amide

溶媒

DMF

反応条件

後処理

1. 1
   温度The mixture was cooled down to rt
2. 2
   抽出the aqueous solution was extracted with EtOAc several times
3. 3
   洗浄washed with brine
4. 4
   乾燥dried (Na2SO4)
5. 5
   その他evaporated in vacuo to an oil
6. 6
   その他The oil was purified by flash column chromatography (96:4:0.4; DCM:MeOH:NH4OH)

実験手順

Following the procedure for converting Compound 1e to Compound 1f, the indazole amide Compound 1e (0.31 g, 17.8 mmol) was treated with 1-bromo-3-methoxypropane (0.3 g, 19.6 mmol) in the presence of 95% NaH (0.05 g, 19.6 mmol) in DMF (50 mL) at 0° C. for 20 min and then warmed to 60° C. for 2 h. The mixture was cooled down to rt. Water was added and the aqueous solution was extracted with EtOAc several times. The organic layers were combined and washed with brine, then dried (Na2SO4) and evaporated in vacuo to an oil. The oil was purified by flash column chromatography (96:4:0.4; DCM:MeOH:NH4OH) to afford a 3-methoxypropyl indazole amide analog of Compound 1f (0.32 g, 73%). 1H NMR (CDCl3) δ 7.69 (d, J=8.13 Hz, 1H), 7.4 (m, 2H), 7.17 (m, 1H), 6.57 (bd s, 1H), 5.39 (bd s, 1H), 4.47 (t, J=6.65 Hz, 2H), 3.96 (s, 2H), 3.30 (t, J=5.78 Hz, 2H), 3.28 (s, 3H), 2.16 (m, 2H). ES-MS m/z 248 (MH+).

出典