HCID 131730655, compound → HCID 57405620, compound

HRID 1260159Notes

Reaction equation

HRID 1260159 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C@H:18]3[C@H:22]([C:23]4[C:33]5=[C:34]6[C:29](=[CH:30][CH:31]=[CH:32]5)[CH2:28][CH2:27][CH2:26][N:25]6[CH:24]=4)[C:21](=[O:35])[NH:20][C:19]3=[O:36])=[CH:14][NH:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:23]1([C@H:22]2[C@H:18]([C:13]3[C:12]4[C:16](=[CH:17][C:9]([OH:8])=[CH:10][CH:11]=4)[NH:15][CH:14]=3)[C:19](=[O:36])[NH:20][C:21]2=[O:35])[C:33]2=[C:34]3[C:29](=[CH:30][CH:31]=[CH:32]2)[CH2:28][CH2:27][CH2:26][N:25]3[CH:24]=1

Participants

5

Reactant 2

HCID 131730655HCID 131730655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57405620HCID 57405620, compoundYield 28.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The (rac)-trans-3-[6-(benzyloxy)-1H-indol-3-yl]-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrrolidine-2,5-dione (500 mg, 1.05 mmol) and 10% Pd/C (10 mg) were stirred under 1 atmosphere of hydrogen in methanol (200 mL) at room temperature for 24 hours. The reaction mixture was filtered through a bed of Celite and the filtrate evaporated to dryness. The residue was purified by silica gel chromatography, eluting with 1-7% methanol in dichloromethane to afford to yield (rac)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-hydroxy-1H-indol-3-yl)pyrrolidine-2,5-dione (117 mg, 28%) as an off-white solid. Mp: 167-170° C.; 1H NMR (DMSO-d6) 400 MHz δ: 11.50 (bs, 1H), 10.62 (s, 1H), 7.32 (s, 1H), 7.13-7.17 (m, 3H), 6.83-6.89 (m, 2H), 6.71 (d, J=1.9 Hz, 1H), 6.48-6.52 (m, 1H), 4.46 (d, J=6.6 Hz, 1H), 4.37 (d, J=6.6 Hz, 1H), 4.01 (s, 2H), 2.89 (s, 2H), 2.09 (s, 2H); LCMS [M+H]: 386.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of Celite
  2. customthe filtrate evaporated to dryness
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 1-7% methanol in dichloromethane
  5. customto afford

Sources & evidence

ORD record
ord-a8784ec445aa4b399e0bfdcac7ab8864
Source dataset
uspto-grants-2013_06
Patent number
US08470786B2

Reaction notes

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