反応式
[CH2:1]([O:8][C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][NH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:24]#[N:25].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[N:12][N:11]([CH:23]([C:24]#[N:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1参加物
実験手順
A solution of dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (1.0 g, 3.45 mmol) and bromo(phenyl)acetonitrile (810 mg, 4.13 mmol) in anhydrous DMF was treated with Cs2CO3 (1.46 g, 4.48 mmol) and stirred at room temperature for 3 days. The solvent was removed in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc several times, and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel using a gradient elution of 0-20% EtOAc/hexanes. Collection and concentration of the appropriate fractions yielded the title product as a yellow oil. 1H NMR (400 MHz, d6-DMSO) δ 7.70 (s, 1H), 7.50-7.45 (m, 3H), 7.43-7.29 (m, 7H), 5.08 (s, 2H), 3.86 (s, 3H), 3.81 (s, 3H); ES MS (M+1)=406.
後処理
- customThe solvent was removed in vacuo
- customthe residue was partitioned between EtOAc and water
- extractionThe aqueous layer was extracted with EtOAc several times
- dry with materialthe combined organic layers were dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by flash column chromatography on silica gel using
- washa gradient elution of 0-20% EtOAc/hexanes
- customCollection and concentration of the appropriate fractions
出典と根拠
- ORDレコード
- ord-051401307b164482b4af2cae00ad380f
- 出典データセット
- uspto-grants-2009_01
- 特許番号
- US07476666B2
関連ノート
読み込み中…