Potassium Carbonate → HCID 70170782, compound

HRID 2171160Notes

Reaction equation

HRID 2171160 reaction equation
[OH:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH2:36])=[O:35])=[CH:32][CH:31]=1>C(#N)C>[CH3:21][O:20][C:3]1[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[O:1][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH2:36])=[O:35])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5842164-(bromomethyl)benzamideHCID 674677565-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

Product 1

HCID 70170782HCID 70170782, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 5-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one (80 mg, 0.279 mmol) in acetonitrile (10 mL) was added potassium carbonate (154 mg, 1.118 mmol) and 4-bromomethyl-benzamide (89 mg, 0.419 mmol) and the resultant reaction mixture was heated to 80° C. for 4 h. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-25% ethyl acetate in pet ether) to afford the title compound as a solid (20 mg, 17%).

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography (silica gel, 0-25% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-d46796c7ea414f94a9ecc4923706fca5
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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