O-Cresol → HCID 67406750, compound

HRID 714725Notes

Reaction equation

HRID 714725 reaction equation
Br[C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH:11]2[CH2:13][CH2:12]2)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:6]1.[C:25]1([CH3:32])[C:30]([OH:31])=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C.[Cu].[Cu]=O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[N:8]([CH:11]3[CH2:13][CH2:12]3)[C:9](=[O:10])[N:5]([CH2:4][C:3]3[CH:21]=[CH:22][CH:23]=[CH:24][C:2]=3[O:31][C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:32])[N:6]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 335O-CresolHCID 67406788HCID 67406788, compound

Product 1

HCID 67406750HCID 67406750, compound

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 23978CopperCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

100 mg (0.25 mmol) of the compound from Example 99A, 53 mg (0.49 mmol) of o-cresol and 91 mg (0.74 mmol) of 4-N,N-dimethylaminopyridine were dissolved in 5 ml of acetonitrile, and 39 mg (0.62 mmol) of copper powder and 49 mg (0.62 mmol) of copper(II) oxide were added. The mixture was stirred at 85° C. for 16 h. For work-up, the mixture was cooled to RT and filtered through silica gel, and the residue was rinsed with a little ethyl acetate. The filtrate was concentrated under reduced pressure and the crude product was then purified chromatographically [Method 19]. This gave 25 mg (23% of theory) of the target compound.

Workup

  1. temperatureFor work-up, the mixture was cooled to RT
  2. filtrationfiltered through silica gel
  3. washthe residue was rinsed with a little ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude product was then purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-90f27c03a3a047fdab8d98a278a6c4c8
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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