Ethyl Acetate → HCID 9884128, compound

HRID 2230031Notes

Reaction equation

HRID 2230031 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14](Br)[CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O.[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>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:19])[CH:25]=3)[CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 9861236HCID 9861236, compound

Product 1

HCID 9884128HCID 9884128, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-benzyl-6-bromo-1,3-dihydro-benzoimidazol-2-one (0.75 g, 2.5 mmol), 3-chloro-phenyl boronic acid (0.4 g, 2.6 mmol), tetrakis(triphenylphosphine)-palladium (0) (0.23 g, 0.2 mmol), and potassium carbonate (0.72 g, 5.2 mmol) in toluene (15 mL) and H2O (8 mL) was subject to a blanket of nitrogen for 15 minutes at 50° C. and then heated to 85° C. for 1 hour. The reaction mixture was cooled to room temperature and ethyl acetate (100 mL) was added. The organic layer was washed twice with aqueous ammonium chloride (30 mL) and once with brine (30 mL), dried over magnesium sulfate and concentrated. After removal of the solvent, the residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane) to give 1-benzyl-6-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one as a white solid (0.134 g, 16%): mp 168-169° C.; 1H-NMR (DMSO-d6) δ 11.0 (s, 1H), 7.66 (t, 1H, J=2.05 Hz), 7.58-7.5 (m, 1H), 7.45 (t, 2H, J=8.18 Hz), 7.37-7.22 (m, 7 H), 7.08 (d, 1H, J=8.18 Hz), 5.1 (s, 2H); MS (ES) m/z 333([M−H]−, 100%); Anal. Calc. For C20H15ClN2O: C, 71.75, H, 4.52, N, 8.37. Found: C, 70.27, H, 4.56, N, 8.0.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed twice with aqueous ammonium chloride (30 mL) and once with brine (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customAfter removal of the solvent
  6. customthe residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d569a27054fd43b4b7644596e4c41812
Source dataset
uspto-grants-2002_07
Patent number
US06423699B1

Reaction notes

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