Carbon tetrabromide → 3-(5-Bromomethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-fluoro-1H-indol-3-yl)pyrrole-2,5-dione

HRID 983995Notes

Reaction equation

HRID 983995 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[C:12](=[O:31])[NH:13][C:14](=[O:30])[C:15]=3[C:16]3[C:26]4=[C:27]5[C:22](=[CH:23][CH:24]=[CH:25]4)[CH2:21][CH:20]([CH2:28]O)[CH2:19][N:18]5[CH:17]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.O>[Br:33][CH2:28][CH:20]1[CH2:21][C:22]2[C:27]3=[C:26]([C:16]([C:15]4[C:14](=[O:30])[NH:13][C:12](=[O:31])[C:11]=4[C:6]4[C:5]5[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=5)[NH:8][CH:7]=4)=[CH:17][N:18]3[CH2:19]1)[CH:25]=[CH:24][CH:23]=2

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22556669HCID 22556669, compound

Product 1

HCID 225567653-(5-Bromomethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-fluoro-1H-indol-3-yl)pyrrole-2,5-dioneYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(6-fluoro-1H-indol-3-yl)-4-(5-hydroxymethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrrole-2,5-dione (500 mg, 1.2 mmol), carbon tetrabromide (796 mg, 2.4 mmol), and triphenylphosphine (314 mg, 1.2 mmol) in 15 mL of dimethylformamide was stirred at room temperature for 6 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (40 mL). The organic layer was washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to reverse phase HPLC to provide 350 mg (61%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (40 mL)
  2. washThe organic layer was washed with saturated aqueous sodium chloride (20 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05b1c43678e847b1a80b60d5863528d2
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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