Water → HCID 46203836, compound

HRID 1641538Notes

Reaction equation

HRID 1641538 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:29][C:30](=[O:32])[CH3:31])([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12](B2OCC(C)(C)CO2)=[CH:11][C:10]=1[Cl:23])(=[O:3])[CH3:2].[Br:33][C:34]1[CH:39]=[CH:38][C:37](I)=[C:36]([F:41])[CH:35]=1.C(=O)([O-])O.[Na+].O>COCCOC>[C:26]([O:25][CH2:24][C:6]([NH:29][C:30](=[O:32])[CH3:31])([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:37]2[CH:38]=[CH:39][C:34]([Br:33])=[CH:35][C:36]=2[F:41])=[CH:11][C:10]=1[Cl:23])(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 57624622HCID 57624622, compound

Product 1

HCID 46203836HCID 46203836, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixed solution of N-{1,1-bis(acetoxymethyl)-3-[2-chloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]propyl}acetamide (2.05 g) of Reference Example 22, 1-bromo-3-fluoro-4-iodobenzene (1.39 g), sodium hydrogen carbonate (2.02 g) and tetrakistriphenylphosphine palladium (51 mg) in 1,2-dimethoxyethane (30 mL)-water (10 mL) was stirred at 100° C. for 9 hr. The reaction mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Pyridine (20 mL) and acetic anhydride (2 mL) were added to the residue, and the mixture was stood at room temperature for one day. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (1.30 g) as white crystals.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionPyridine (20 mL) and acetic anhydride (2 mL) were added to the residue
  6. additionWater was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. washthe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5564e1b908ad4c9a89c1ffd3f566dd78
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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