HCID 72545728, compound → HCID 72545729, compound

HRID 1483191Notes

Reaction equation

HRID 1483191 reaction equation
[Br:1][C:2]1[C:3]([CH3:23])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1>CCO.C(O)(=O)C.[Fe]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:5]2[C:4]3[C:9](=[CH:10][C:11]([CH3:12])=[C:2]([Br:1])[C:3]=3[CH3:23])[O:8][C:7](=[O:13])[CH:6]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 1

HCID 72545728HCID 72545728, compound

Product 1

HCID 72545729HCID 72545729, compoundYield 0.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of the crude material (22 mg) containing 6-bromo-5,7-dimethyl-4-(4-nitrophenyl)-2H-chromen-2-one (7-2) in EtOH (0.75 mL) and acetic acid (0.15 mL) was added iron (16 mg, 0.29 mmol) at room temperature. The mixture was heated at 110° C. for 2.5 h. The reaction mixture was then cooled at room temperature and filtrated. To the filtrate was added EtOAc and saturated NaHCO3 solution, and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. The residues was purified by silica gel column chromatography (hexane:EtOAc=5:1˜2:1) to give the title compound 7-3 (4.0 mg, 0.8% yield, 2 steps) as an orange solid.

Workup

  1. temperatureThe reaction mixture was then cooled at room temperature
  2. filtrationfiltrated
  3. additionTo the filtrate was added EtOAc and saturated NaHCO3 solution
  4. extractionextracted with EtOAc
  5. washThe organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residues was purified by silica gel column chromatography (hexane:EtOAc=5:1˜2:1)

Sources & evidence

ORD record
ord-2bdc589d930443d994e71d23e94b7789
Source dataset
uspto-grants-2016_08
Patent number
US09416121B2

Reaction notes

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