Ethyl Acetate → HCID 59783752, compound

HRID 1946643Notes

Reaction equation

HRID 1946643 reaction equation
Cl[C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[N:5]([CH3:10])[C:6](=[O:9])[CH2:7][N:8]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].[C:28](=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][N:5]1[C:4]2[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=2[C:2]([C:22]2[CH:23]=[CH:24][C:19]([C:17]([O:16][CH2:15][CH3:28])=[O:18])=[CH:20][CH:21]=2)=[N:8][CH2:7][C:6]1=[O:9]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 11820387HCID 11820387, compound

Product 1

HCID 59783752HCID 59783752, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Title compound 468 (1.69 g, 8.10 mmol) was dissolve in DME (50 mL) and 4-(methoxycarbonyl)phenylboronic acid (1.47 g, 7.58 mmol) was added followed by tetrakis(triphenylphosphine) palladium (0) (0.301 g, 0.260 mmol) and then sodium carbonate (2M in water, 12 mL, 24.00 mmol). The reaction mixture was stirred at 90° C. for 1 h, cooled at room temperature and poured into ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by flash chromatography (10% ethyl acetate in hexanes) to afford title compound 469 (1.41 g, 54%) as a red foam. MS (ESI): 323.42 (MH)+.

Workup

  1. temperaturecooled at room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b3090c0b78ec4f3487583144e9c8de98
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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