Carbon tetrabromide → HCID 69270863, compound

HRID 751512Notes

Reaction equation

HRID 751512 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[C:16](=[O:32])[NH:17][C:18](=[O:31])[C:19]=2[C:20]2[C:28]3[O:27][CH:26]=[CH:25][C:24]=3[C:23]([O:29][CH3:30])=[CH:22][CH:21]=2)=[CH:7]1.C(Br)(Br)(Br)[Br:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:34][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[C:16](=[O:32])[NH:17][C:18](=[O:31])[C:19]=2[C:20]2[C:28]3[O:27][CH:26]=[CH:25][C:24]=3[C:23]([O:29][CH3:30])=[CH:22][CH:21]=2)=[CH:7]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69270073HCID 69270073, compound

Product 1

HCID 69270863HCID 69270863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3-[1-(4-hydroxybutyl)-1H-indol-3-yl]-4-(4-methoxybenzofur-7-yl)pyrrole-2,5-dione (0.1 g, 0.232 mmol) in 10 mL dichloromethane. Add carbon tetrabromide (0.077 g, 1 equivalent) and triphenyl phosphine (0.061 g, 1 equivalent). Stir for 10 min, add another equivalent of both reagents. Stir 10 min then dilute with dichloromethane and wash with water followed by brine. Dry over magnesium sulfate then filter and concentrate. Purification by column chromatography (2% methanol: dichloromethane) affords the title compound. MS (ES, m/z): 493.0 (M−1).

Workup

  1. additionadd another equivalent of both reagents
  2. stirringStir 10 min
  3. washwash with water
  4. dry with materialDry over magnesium sulfate
  5. filtrationthen filter
  6. concentrationconcentrate
  7. customPurification by column chromatography (2% methanol: dichloromethane)

Sources & evidence

ORD record
ord-5f62953285e741e58084c21f20d29efe
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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