Sodium Carbonate → HCID 18630100, compound

HRID 378078Notes

Reaction equation

HRID 378078 reaction equation
[Cl:1][C:2]1[C:12](I)=[CH:11][CH:10]=[C:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:11][CH:10]=[C:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic AcidHCID 10523923HCID 10523923, compound

Product 1

HCID 18630100HCID 18630100, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound of Example 239 (0.191 g, 0.5 mmol) and palladium tetrakistriphenylphosphine (23 mg, 0.02 mmol) in toluene (10 mL) was added 2 M sodium carbonate (0.5 mL) and phenyl boronic acid (73 mg, 0.6 mmol). The mixture was heated at 90° C. for 30 h, additional portions of catalyst (20 mg) and 2 M sodium carbonate (0.5 mL) were added and heating was continued for 24 h. The cool reaction was diluted with CH2Cl2 and washed with 2 M sodium carbonate (50 mL with 5 mL conc NH4OH). The organic layer was dried (MgSO4) and concentrated. The crude product was purified by RC (ethyl acetate/hexanes) and recrystallization from hexanes to afford the title compound as white needles (98 mg, 59%). m.p. 134-135° C.

Workup

  1. temperatureheating
  2. customThe cool reaction
  3. washwashed with 2 M sodium carbonate (50 mL with 5 mL conc NH4OH)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by RC (ethyl acetate/hexanes) and recrystallization from hexanes

Sources & evidence

ORD record
ord-9baeb74ed61444329b7f549e177391ea
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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