Potassium Carbonate → HCID 67467179, compound

HRID 2171194Notes

Reaction equation

HRID 2171194 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:7]([OH:24])=[C:8]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH2:16][CH2:17][C:18]4=[O:23])[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][C:33]([NH:35][CH2:36][CH2:37][CH3:38])=[O:34]>C(#N)C>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH2:16][CH2:17][C:18]4=[O:23])[C:7]=2[O:24][CH2:32][C:33]([NH:35][CH2:36][CH2:37][CH3:38])=[O:34])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2207962-Bromo-N-propylethanimidic acidHCID 67465433HCID 67465433, compound

Product 1

HCID 67467179HCID 67467179, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-(3-(cyclopropylmethoxy)-2-hydroxy-4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one (100 mg, 0.308 mmol) in acetonitrile (15 mL) was added potassium carbonate (127 mg, 0.925 mmol) and 2-bromo-N-propylacetamide (110 mg, 0.616 mmol) and the resultant reaction mixture was heated to 70° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-45% ethyl acetate in pet ether) to afford the title compound as a solid (40 mg, 30.7%).

Workup

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, 0-45% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-84b8256c1cc6487f913e38b9c7250d39
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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