Indole-3-acetamide → 3-(1H-Indol-3-yl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-7-yl]-pyrrole-2,5-dione

HRID 2215762Notes

Reaction equation

HRID 2215762 reaction equation
CC([O-])(C)C.[K+].C1COCC1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]([NH2:24])=[O:23])=[CH:13]1.C[O:26][C:27](=O)[C:28]([C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[N:37]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:36]=[CH:35]2)=O>CN(C=O)C>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[C:22](=[O:23])[NH:24][C:27](=[O:26])[C:28]=2[C:30]2[CH:31]=[CH:32][CH:33]=[C:34]3[C:38]=2[N:37]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:36]=[CH:35]3)=[CH:13]1

Participants

6

Reactant 4

HCID 397Indole-3-acetamideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 69641843{1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-7-yl}-oxo-acetic acid methyl ester

Product 1

HCID 219500793-(1H-Indol-3-yl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-7-yl]-pyrrole-2,5-dioneYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1.0 M solution of KOtBu in THF (8.1 mL, 8.1 mmol) was added to a solution of 2-(1H-indol-3-yl)-acetamide (417 mg, 2.4 mmol) and {1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-7-yl}-oxo-acetic acid methyl ester (774 mg, 2.32 mmol) in DMF (50 mL). The deep red-orange solution was stirred 16 h at room temperature and then 1 h at 65° C. The heating bath was removed and pH 7.0 buffer added. The mixture was poured into EtOAc, the layers separated and the EtOAc solution washed with 0.1 N HCl, water (3×), saturated aq NaHCO3 and brine (3×), dried (MgSO4), filtered and concentrated onto SiO2. Flash chromatography afforded 3-(1H-Indol-3-yl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-7-yl]-pyrrole-2,5-dione (141 mg, 13%) as a bright orange solid which was dried under vacuum overnight at 70° C., and 3-(1H-Indol-7-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (165 mg, 22%) as a bright red solid which was dried under vacuum overnight at 70° C.

Workup

  1. custom1 h
  2. customat 65° C
  3. customThe heating bath was removed
  4. additionThe mixture was poured into EtOAc
  5. customthe layers separated
  6. washthe EtOAc solution washed with 0.1 N HCl, water (3×), saturated aq NaHCO3 and brine (3×)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated onto SiO2

Sources & evidence

ORD record
ord-1c95a2dee82f475bab27eac137f5efed
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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