Sodium Carbonate → HCID 18630100, compound

HRID 725545Notes

Reaction equation

HRID 725545 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 2M 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 2M sodium carbonate (0.5 mL) were added and heating was continued for 24 h. The cool reaction was diluted with CH2Cl2 and washed with 2M 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 2M 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-520ee34ebf124f278f646d1f971836bd
Source dataset
uspto-grants-1998_01
Patent number
US05705513

Reaction notes

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