Ethyl Acetate → HCID 59408986, compound

HRID 1894746Notes

Reaction equation

HRID 1894746 reaction equation
[C:1]1([C:12]2[C:13](=[O:27])[NH:14][C:15](=[O:26])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[C:9]2[C:4]3=[C:5]([CH2:10][CH2:11][N:3]3[CH:2]=1)[CH:6]=[CH:7][CH:8]=2.[Mg].C(OCC)(=O)C>CO>[C:1]1([C@H:12]2[C@H:16]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[C:15](=[O:26])[NH:14][C:13]2=[O:27])[C:9]2[C:4]3=[C:5]([CH2:10][CH2:11][N:3]3[CH:2]=1)[CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5462224MagnesiumHCID 59408991HCID 59408991, compound

Product 1

HCID 59408986HCID 59408986, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (115 mg, 0.33 mmol) in anhydrous methanol (10 ml) was added magnesium turnings (200 mg). The mixture was heated to reflux for 1.5 hours. The mixture was cooled to room temperature poured into ethyl acetate (100 ml) washed with 1M hydrochloric acid (100 ml) and dried over anhydrous magnesium sulfate. Evaporation to dryness gave a residue that was purified by flash column chromatography (SiO2, 50% EtOAc in hexanes) to yield (±)-trans-3-(4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione as a pink solid (108 mg). M.p.=144-148° C., 400 MHz 1H NMR (DMSO-d6) δ: 11.53 (s, 1H), 11.05 (s, 1H), 7.41-7.35 (m, 4H), 7.14-7.07 (m, 2H), 6.96 (t, J=7.6 Hz, 1H), 6.89-6.85 (m, 2H), 4.51-4.45 (m, 4H), 3.69 (t, J=7.2 Hz, 2H); LCMS: 356 [M+H].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. washwashed with 1M hydrochloric acid (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation to dryness
  6. customgave a residue that
  7. customwas purified by flash column chromatography (SiO2, 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c2feab467f234d199799593d159317d3
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

Loading…