Water → HCID 23114118, compound

HRID 2376586Notes

Reaction equation

HRID 2376586 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([CH3:13])=[C:4]([NH:14][C:15](=[O:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:3]=1[CH3:22].[CH:23]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].O>N1C=CC=CC=1.[Cu](I)I>[CH:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:2]2[C:10]3[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=3[C:5]([CH3:13])=[C:4]([NH:14][C:15](=[O:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:3]=2[CH3:22])=[CH:28][CH:27]=1)([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 74654-IsopropylphenolHCID 11430Potassium CarbonateHCID 23114116HCID 23114116, compound

Product 1

HCID 23114118HCID 23114118, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

A mixed solution of N-(7-bromo-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.36 mmol) obtained in Example 343, 4-isopropylphenol (556 mg, 4.08 mmol) and potassium carbonate (188 mg, 1.36 mmol) in pyridine (16 mL) was stirred at 140° C. under argon atmosphere for 1 hour. Copper iodide (259 mg, 1.36 mmol) was added to the reaction solution and the mixture was stirred at 140° C. for 60 hours. Water was added to the reaction solution and the product was extracted with ethyl acetate. The combined organic layers were washed with 1 N hydrochloric acid and an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) and Gilson HPLC to obtain 230 mg (yield: 40%) of the title compound. Melting point: 148-149° C. (ethyl acetate-hexane).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined organic layers were washed with 1 N hydrochloric acid
  3. dry with materialan aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) and Gilson HPLC

Sources & evidence

ORD record
ord-e32fb6e3dd4846a19c5dcb71755cd760
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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