Boron tribromide → HCID 69268944, compound

HRID 751537Notes

Reaction equation

HRID 751537 reaction equation
C[O:2][C:3]1[C:8]2[CH:9]=[CH:10][O:11][C:7]=2[C:6]([C:12]2[C:13](=[O:31])[NH:14][C:15](=[O:30])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][CH2:27][CH2:28][OH:29])[CH:18]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]2[CH:9]=[CH:10][O:11][C:7]=2[C:6]([C:12]2[C:13](=[O:31])[NH:14][C:15](=[O:30])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][CH2:27][CH2:28][OH:29])[CH:18]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69270973HCID 69270973, compound

Product 1

HCID 69268944HCID 69268944, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-(4-methoxybenzofur-7-yl)-4-[1-(3-hydroxypropyl)-1H-indol-3-yl]pyrrole-2,5-dione (0.1 g, 0.24 mmol) in 2.5 mL dichloromethane under nitrogen at −78° C. Add boron tribromide (0.11 mL, 1.16 mmol, 5 equiv) dropwise and stir at −78° C. for 1 hr, warm to room temperature and stir for 1 hr. Quench the reaction with ice and then extract with ethyl acetate. Washed the organics with brine, dry over sodium sulfate, filter, and concentrate in vacuo. Purification by column chromatography (25% ethyl acetate: hexanes to 50% ethyl acetate: hexanes) afforded 0.050 g (52%) of the title product. High Res. Mass Spec (m/z): Calcd 403.1301 Found 403.1294.

Workup

  1. customQuench
  2. customthe reaction with ice
  3. extractionextract with ethyl acetate
  4. washWashed the organics with brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurification by column chromatography (25% ethyl acetate: hexanes to 50% ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-6a7d591a3ecd45069a82e0fd7a675285
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

Loading…