Hydrogen Bromide → HCID 44624415, compound

HRID 2390799Notes

Reaction equation

HRID 2390799 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[C:14]([C:16]3[C:17]([O:22]C)=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=2[O:28][CH3:29])=[O:9])[CH:5]=[CH:6][CH:7]=1.Br.C([O-])(O)=O.[Na+]>CC(O)=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8]([C:10]1[CH:15]=[C:14]([C:16]2[C:17](=[O:22])[NH:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=1[O:28][CH3:29])=[O:9]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 67069865HCID 67069865, compound

Product 1

HCID 44624415HCID 44624415, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

step 3—A solution of 36 (69 mg, 0.177 mmol), 48% HBr (0.075 mL, 0.654 mmol) and AcOH (3 mL) in a sealed tube was heated overnight at 60° C. The reaction mixture was cooled to RT, carefully poured into a cold saturated aqueous NaHCO3 solution 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 EtOAc/hexanes to afford 44 mg (66% yield) of 3-[3-(3-amino-benzoyl)-5-tert-butyl-4-methoxy-phenyl]-1H-pyridin-2-one (38 [I-59]) as a light yellow 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

Sources & evidence

ORD record
ord-0934f5c7eb5a42be82cad5e9d12f7d08
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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