2-(1-Methyl-1H-indol-3-yl)acetamide → 3-(1-benzofuran-3-yl)-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

HRID 222480ノート

反応式

HRID 222480 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([NH2:14])=[O:13])=[CH:3]1.C([O:17][C:18](=O)[C:19]([C:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[O:23][CH:22]=1)=O)C.C(O[K])(C)(C)C>C1COCC1>[O:23]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:21]([C:19]2[C:18](=[O:17])[NH:14][C:12](=[O:13])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:22]1

参加物

5

反応物 3

HCID 153579072-(1-Methyl-1H-indol-3-yl)acetamideHCID 59140672Ethyl 2-(benzofuran-3-yl)-2-oxoacetateHCID 178418922HCID 178418922、化合物

生成物 1

HCID 53276643-(1-benzofuran-3-yl)-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione収率 45.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of commercially available 2-(1-Methyl-1H-indol-3-yl)-acetamide (54 mg, 0.28 mmol) and benzofuran-3-yl-oxo-acetic acid ethyl ester (63 mg, 0.28 mmol) in dry THF (2.5 mL) at 0° C. was added dropwise a 1.0 M solution of tert-BuOK in THF (1.15 mL), and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched with 12 N HCl and diluted with EtOAc. The organic solution was washed with saturated NaHCO3, brine, then dried over Na2SO4, evaporated in vacuo and purified by preparative TLC (ethyl acetate:hexane; 2:3) to afford product 3-benzofuran-3-yl-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (1) (44 mg, 44%) as an orange solid.

後処理

  1. customThe reaction mixture was quenched with 12 N HCl
  2. additiondiluted with EtOAc
  3. washThe organic solution was washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. custompurified by preparative TLC (ethyl acetate:hexane; 2:3)

出典と根拠

ORDレコード
ord-8e36f115c977484a8c53021283d99f0d
出典データセット
uspto-grants-2012_06
特許番号
US08207216B2

反応ノート

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