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 222480Notes

Reaction equation

HRID 222480 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8e36f115c977484a8c53021283d99f0d
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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