Carbon tetrabromide → HCID 17985596, compound

HRID 910129Notes

Reaction equation

HRID 910129 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[O:25][CH:24]=[CH:23][C:22]=3[C:21]([O:27][CH2:28][CH2:29][CH2:30]O)=[CH:20][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.C(Br)(Br)(Br)[Br:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[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[O:25][CH:24]=[CH:23][C:22]=3[C:21]([O:27][CH2:28][CH2:29][CH2:30][Br:35])=[CH:20][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

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 17985613HCID 17985613, compound

Product 1

HCID 17985596HCID 17985596, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]-quinolin-1-yl)-4-(4-(3-(hydroxy)propoxy)benzofur-7-yl)-2,5-dioxopyrrole (0.1 g, 0.232 mmol) in 10 mL dichloromethane. Add carbon tetrabromide (0.077 g) and triphenylphosphine (0.061 g). Stir for 10 minutes and add another equivalent of both reagents. Stir 10 minutes then dilute with dichloromethane and wash with water followed by saturated aqueous sodium chloride. Dry over magnesium sulfate then filter and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with 2% methanol in dichloromethane to provide the desired compound (0.116 g)

Workup

  1. additionadd another equivalent of both reagents
  2. stirringStir 10 minutes
  3. washwash with water
  4. dry with materialDry over magnesium sulfate
  5. filtrationthen filter
  6. concentrationconcentrate under reduced pressure
  7. washSubject residue to silica gel chromatography, eluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-945e6101906a45dfb73260d34bc1554e
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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