Carbon tetrabromide → HCID 22556832, compound

HRID 983986Notes

Reaction equation

HRID 983986 reaction equation
[C:1]1([C:13]2[C:14](=[O:33])[NH:15][C:16](=[O:32])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][CH2:29][CH2:30]O)[CH:19]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:54]>ClCCl>[Br:54][CH2:30][CH2:29][CH2:28][CH2:27][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([C:17]2[C:16](=[O:32])[NH:15][C:14](=[O:33])[C:13]=2[C:1]2[C:11]3=[C:12]4[C:7](=[CH:8][CH:9]=[CH:10]3)[CH2:6][CH2:5][CH2:4][N:3]4[CH:2]=2)=[CH:19]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22556843HCID 22556843, compound

Product 1

HCID 22556832HCID 22556832, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-[1-(4-hydroxybutyl)-1H-indol-3-yl]pyrrole-2,5-dione (0.11 g, 0.25 mmol) and triphenylphosphine (0.08 g, 0.31 mmol) in dichloromethane (3 mL) was treated with carbon tetrabromide (0.095 g, 0.286 mmol) and stirred for 3 hours. The reaction mixture was then concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with 2% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.101 g (80%) of the title compound as a dark red foam.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. washeluting with 2% methanol in dichloromethane
  3. additionFractions containing product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df6323dc1a924418910b5827c2c516bf
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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