Boron tribromide → HCID 57595565, compound

HRID 1785596Notes

Reaction equation

HRID 1785596 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=3)[NH:13][CH:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:18]=3)[NH:13][CH:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57595741HCID 57595741, compound

Product 1

HCID 57595565HCID 57595565, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 293 (26.6 mg, 0.079 mmol) was dissolved in methylene chloride (10 mL) under an atmosphere of nitrogen. Into the reaction mixture was added 1.0 M boron tribromide in methylene chloride (0.3 mL). The reaction was stirred at room temperature overnight. The solvent evaporated over time, so methylene chloride (10 mL) was added, followed by 1.0 M boron tribromide in methylene chloride (0.6 mL). The reaction was stirred overnight. The reaction was quenched with methanol (10 mL), concentrated under reduced pressure, and extracted with brine and ethyl acetate. The organic portion was dried with anhydrous magnesium sulfate and concentrated to dryness to provide a yellow solid. The material was purified by prep TLC (5% methanol:methylene chloride). The appropriate band was scraped and the compound eluted from the silica with ethyl acetate. The mixture was filtered and the filtrate concentrated to provide compound 294 as a yellow solid as identified by 1H-NMR and MS (1.2 mg, LRMS (ESI) [M+H+]+=330.1).

Workup

  1. customThe solvent evaporated over time, so methylene chloride (10 mL)
  2. additionwas added
  3. stirringThe reaction was stirred overnight
  4. customThe reaction was quenched with methanol (10 mL)
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with brine and ethyl acetate
  7. dry with materialThe organic portion was dried with anhydrous magnesium sulfate
  8. concentrationconcentrated to dryness
  9. customto provide a yellow solid
  10. customThe material was purified by prep TLC (5% methanol:methylene chloride)
  11. washthe compound eluted from the silica with ethyl acetate
  12. filtrationThe mixture was filtered
  13. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-4fd4253ff2664922b766e3523de10f2e
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

Loading…