反応式
F[C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=C3/C=C(C4C=CC(C=O)=CC=4)C(C)(C)O/3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.N1(CCOCCO)CCNCC1.C([BH3-])#N.[Na+].C1COCC1.C([O-])(O)=O.[Na+]>CN(C=O)C.CO.O.CC(O)=O>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[CH:2][CH:10]=2)[CH2:6][C:7]1=[O:11]参加物
反応物 5
生成物 1
試薬・触媒・溶媒 4
実験手順
A mixture of 4-[(5E)-5-(6-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2,2-dimethyl-2,5-dihydrofuran-3-yl]benzaldehyde (55 mg, 0.16 mmol), 2-(2-(piperazin-1-yl)ethoxy)ethanol (56 mg, 0.32 mmol) and 4 Å molecular sieves (100 mg) in anhydrous DMF (3 mL) was stirred at room temp for 16 hours. To this stirred mixture was added AcOH (10 mg), 1M sodium cyanoborohydride in THF solution (0.32 mL, 0.32 mmol) and 3 mL of anhydrous methanol. The reaction mixture was stirred at room temp for 5 hours and poured into 100 mL of water. Saturated NaHCO3 solution was then added until pH=9. The precipitates were filtered, washed with water, and dried in vacuo to give the crude product, which was purified through silica gel column with 5-10% MeOH/CHCl3 to give (3E)-6-fluoro-3-{4-[4-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}methyl)phenyl]-5,5-dimethylfuran-2(5H)-ylidene}-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 45 mg, 56%.
後処理
- stirringThe reaction mixture was stirred at room temp for 5 hours
- filtrationThe precipitates were filtered
- washwashed with water
- customdried in vacuo
- customto give the crude product, which
- customwas purified through silica gel column with 5-10% MeOH/CHCl3
出典と根拠
- ORDレコード
- ord-49d1d9f1fd744d679a52a3e18e301cb5
- 出典データセット
- uspto-grants-2013_02
- 特許番号
- US08367664B2
関連ノート
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