Boron tribromide → HCID 24962572, compound

HRID 1522833Notes

Reaction equation

HRID 1522833 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([C:14]#[N:15])[CH:8]=[C:9]([O:12]C)[CH:10]=2)[C:5](=[O:16])[N:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[CH:3]=1.B(Br)(Br)Br>O>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([C:14]#[N:15])[CH:8]=[C:9]([OH:12])[CH:10]=2)[C:5](=[O:16])[N:4]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24962571HCID 24962571, compound

Product 1

HCID 24962572HCID 24962572, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-6-methoxy-2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-8-carbonitrile (0.15 g, 0.39 mmol) was placed in a dry and argon flushed 100 mL single-necked round-bottomed flask fitted with a stirring bar, reflux condenser and an argon inlet. Anhydrous chlorobenzene (10 mL) was added via a syringe at room temperature. BBr3 (0.59, 2.33 mmol) was added via a syringe with stirring at room temperature. The resulting solution was heated to 120° C. for 4 hours. 10 mL of water was added to quench the reaction. After stirred at room temperature for one hour, the solution was extracted with EtOAc (5×20 mL). The organic layers were combined and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica-gel, CH2C2/MeOH=9/1 v/v) to give a white solid product, 0.05 g, 36.0% yield. M.p. ° C. (decomposed). MS: m/z 357.1 [M+H]+. 1H NMR (DMSO-d6, 300 MHz) δ 11.40 (s, 1H), 9.79 (s, 1H), 7.91 (s, 1H), 7.48 (d, 1H, J=2.1 Hz), 7.38 (d, 1H, J=2.1 Hz), 7.26 (d, 2H, J=8.7 Hz), 6.86 (d, 2H, J=8.7 Hz).

Workup

  1. customa dry
  2. customargon flushed 100 mL single-necked round-bottomed flask
  3. customfitted with a stirring bar
  4. temperaturereflux condenser and an argon inlet
  5. additionAnhydrous chlorobenzene (10 mL) was added via a syringe at room temperature
  6. temperatureThe resulting solution was heated to 120° C. for 4 hours
  7. customto quench
  8. customthe reaction
  9. stirringAfter stirred at room temperature for one hour
  10. extractionthe solution was extracted with EtOAc (5×20 mL)
  11. dry with materialdried over anhydrous MgSO4
  12. customThe solvent was removed under reduced pressure
  13. customThe residue was purified by column chromatography (silica-gel, CH2C2/MeOH=9/1 v/v)
  14. customto give a white solid product, 0.05 g, 36.0% yield

Sources & evidence

ORD record
ord-03872bdbb69b4eafbe30af24171def79
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

Loading…