Indole-3-acetamide → 3(1-methyl-5-methoxy-1H-indol-7-yl)-4-(1H-indol-3-yl]-pyrrole-2,5-dione

HRID 2215785Notes

Reaction equation

HRID 2215785 reaction equation
CO[C:3](=[O:18])[C:4]([C:6]1[CH:7]=[C:8]([O:16][CH3:17])[CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[CH:12]=[CH:11]2)=O.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][C:29]([NH2:31])=[O:30])=[CH:20]1.CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[CH3:15][N:13]1[C:14]2[C:10](=[CH:9][C:8]([O:16][CH3:17])=[CH:7][C:6]=2[C:4]2[C:3](=[O:18])[NH:31][C:29](=[O:30])[C:28]=2[C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)[CH:11]=[CH:12]1

Participants

6

Reactant 4

HCID 397Indole-3-acetamideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 69642138(1-methyl-5-methoxy-1H-indol-7-yl)-oxo-acetic acid methyl ester

Product 1

HCID 219500303(1-methyl-5-methoxy-1H-indol-7-yl)-4-(1H-indol-3-yl]-pyrrole-2,5-dioneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of (1-methyl-5-methoxy-1H-indol-7-yl)-oxo-acetic acid methyl ester (0.27 g, 1.1 mmol) and 2-(1H-indol-3-yl-acetamide (0.17 g, 1 mmol) in DMF (5 mL) was added a solution of potassium tert-butoxide in THF (1.0 M, 4 mL, 4 mmol) at room temperature. The reaction mixture was heated at 50° C. for 7 h, cooled to room temperature, quenched with water, and the mixture extracted with ethyl acetate. The extract was washed with water, saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate), filtered and concentrated. Flash column chromatography on silica gel eluting with chloroform and acetone gave 3(1-methyl-5-methoxy-1H-indol-7-yl)-4-(1H-indol-3-yl]-pyrrole-2,5-dione (210 mg, 56.5%). 1H NMR (d6-DMSO, 400 MHz) 3.52 (s, 3H), 3.56 (s, 3H), 6.35˜6.46 (m, 1H), 6.28 (d, J=2.93 Hz, 1H), 6.41 (t, J=2.44 Hz, 1H), 6.88 (t, J=6.84 Hz, 1H), 7.02 (d, J=2.44 Hz, 1H), 7.10 (d, J=3.42 Hz, 1H), 7.24 (d, J=7.82, 1H), 7.80 (d, J=2.93, 1H), 11.03 (s, 1H), 11.76 (m, 1H); MS (ES, m/z): C22H17N3O3: 372.2 (M++1); 370.3 (M+−1).

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe extract was washed with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29f01a0018724e2aa7cdd48a00a4aab1
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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