Hydrogen Bromide → HCID 44624285, compound

HRID 2390833Notes

Reaction equation

HRID 2390833 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([C:18]2[C:19]([O:24]C)=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C([O-])(O)=O.[Na+]>CC(O)=O>[CH2:1]([C:8]1[CH:9]=[C:10]([C:18]2[C:19](=[O:24])[NH:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 67069899HCID 67069899, compound

Product 1

HCID 44624285HCID 44624285, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

step 2—A solution of 126 (156 mg, 0.471 mmol), 48% HBr (150 □L, 1.30 mmol) and HOAc (4 mL) in sealed tube was heated overnight at 70° C. The reaction mixture was cooled to RT, carefully poured into a cold saturated aqueous NaHCO3 and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified on a preparative SiO2 TLC plate developed with 66% EtOAc/hexanes to afford 124 mg (83%) of I-46 as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified on a preparative SiO2 TLC plate
  7. customto afford 124 mg (83%) of I-46 as a white solid

Sources & evidence

ORD record
ord-4f1dfe6d7a3e4d1f84980c9776fcc1ea
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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