Ethyl Acetate → HCID 59783752, compound

HRID 718113Notes

Reaction equation

HRID 718113 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-bf75d194e2c945eb9a8887992242dade
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

Loading…