Pyridine → 3-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzaldehyde

HRID 1594865Notes

Reaction equation

HRID 1594865 reaction equation
[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:10])[CH3:2].[CH:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19].N1C=CC=C[CH:30]=1>C(Cl)Cl>[CH2:1]([C:3]1([C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[O:17][C:24]2[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=2)[CH:18]=[O:19])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:30])[C:4]1=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27343563-Formylphenylboronic acidHCID 217062193-Ethyl-3-(3-hydroxy-phenyl)-azepan-2-one

Product 1

HCID 217062123-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one (as described in Example 8, Step B) (0.10 g, 0.4 mmol), 3-formylphenyl-boronic acid (0.12 g, 0.8 mmol), cupric acetate (0.073 g, 0.4 mmol) and powdered 4A molecular sieves (0.12 g) were combined under Ar, diluted with anhydrous CH2Cl2 (2 mL) and pyridine (0.162 mL, 2.0 mmol) and stirred at ambient temperature for 48 hrs. The reaction mixture was filtered, and the filtrated concentrated to dryness and partitioned between EtOAc and H2O. The aqueous layer was washed with EtOAc, the organics combined, washed with H2O, 10% aqueous NaOH solution, H2O, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound as a white solid after trituration with diethyl ether/hexane.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrated concentrated to dryness
  3. custompartitioned between EtOAc and H2O
  4. washThe aqueous layer was washed with EtOAc
  5. washwashed with H2O, 10% aqueous NaOH solution, H2O, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-c295a5772c4246c59864fad6eaa3091c
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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