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 222480노트

반응식

HRID 222480 반응식
[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

참가 물질

5

반응물 3

HCID 153579072-(1-Methyl-1H-indol-3-yl)acetamideHCID 59140672Ethyl 2-(benzofuran-3-yl)-2-oxoacetateHCID 178418922HCID 178418922, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8e36f115c977484a8c53021283d99f0d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207216B2

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