Magnesium → HCID 57405619, compound

HRID 1260162Notes

Reaction equation

HRID 1260162 reaction equation
[OH:1][CH:2]1[C:11]2[C:6]3=[C:7]([C:12]([C:14]4[C:15](=[O:29])[NH:16][C:17](=[O:28])[C:18]=4[C:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[NH:21][CH:20]=4)=[CH:13][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2.[Mg]>CO>[OH:1][CH:2]1[C:11]2[C:6]3=[C:7]([C:12]([C@H:14]4[C@H:18]([C:19]5[C:27]6[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=6)[NH:21][CH:20]=5)[C:17](=[O:28])[NH:16][C:15]4=[O:29])=[CH:13][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 67980614HCID 67980614, compound

Product 1

HCID 57405619HCID 57405619, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(6-hydroxy-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione (293 mg, 0.76 mmol) in anhydrous methanol (15 mL) in a 40 mL reaction vial was added magnesium turnings (300 mg, 15.2 mmol). The mixture was capped and heated at 80° C. in an oil bath. After 4 hr the reaction was cooled to room temperature and the methanol removed under reduced pressure. The mixture was diluted with dichloromethane (20 mL) and washed with 10% HCl (20 mL). The aqueous layer was extracted with dichloromethane (3×20 mL), washed with brine, dried over sodium sulfate, and concentrated to dryness. The residue was purified by silica gel chromatography, eluting with a methanol/dichloromethane (1-5%) to afford (rac)-trans-3-(6-hydroxy-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione as a off-white solid (42 mg, 14%). Mp: 153-155° C.; 1H NMR (DMSO-d6) 400 MHz δ: 11.54 (bs, 1H), 11.04 (bs, 1H), 7.42-7.35 (m, 4H), 7.26 (d, J=7.8 Hz, 1H), 7.04-7.08 (m, 2H), 6.98-6.93 (m, 2H), 5.34 (brs, 1H), 4.88 (brs, 1H), 4.55 (d, J=6.6 Hz, 1H), 4.49 (d, J=6.6 Hz, 1H), 4.13 (s, 2H), 2.10 (s, 2H); LCMS [M+H]: 386.

Workup

  1. customThe mixture was capped
  2. temperatureAfter 4 hr the reaction was cooled to room temperature
  3. customthe methanol removed under reduced pressure
  4. additionThe mixture was diluted with dichloromethane (20 mL)
  5. washwashed with 10% HCl (20 mL)
  6. extractionThe aqueous layer was extracted with dichloromethane (3×20 mL)
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with a methanol/dichloromethane (1-5%)

Sources & evidence

ORD record
ord-9c73d5322fcc41ca879fa1e5af063511
Source dataset
uspto-grants-2013_06
Patent number
US08470786B2

Reaction notes

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