Water → HCID 46203835, compound

HRID 1641528Notes

Reaction equation

HRID 1641528 reaction equation
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3([NH:24][C:25](=[O:27])[CH3:26])[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]3)=[CH:10][CH:9]=2)OC1.[Br:29][C:30]1[CH:35]=[CH:34][C:33](I)=[C:32]([F:37])[CH:31]=1.C(=O)([O-])O.[Na+].O>COCCOC.C(OC(C)C)(C)C>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]3([NH:24][C:25](=[O:27])[CH3:26])[CH2:17][O:18][C:19]([CH3:23])([CH3:22])[O:20][CH2:21]3)=[CH:12][CH:13]=2)=[C:32]([F:37])[CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzene2×HCID 57624582HCID 57624582, compound

Product 1

HCID 46203835HCID 46203835, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixed solution of N-(5-{2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide (7.33 g) of Reference Example 6, 1-bromo-3-fluoro-4-iodobenzene (5.95 g), sodium hydrogen carbonate (9.48 g) and tetrakistriphenylphosphine palladium (434 mg) in 1,2-dimethoxyethane (120 mL)-water (40 mL) was heated under reflux for 8 hr. 1-Bromo-3-fluoro-4-iodobenzene (2.83 g) and tetrakistriphenylphosphine palladium (217 mg) were added to the reaction mixture, and the mixture was further stirred at 100° C. for 15 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 and the residue was purified by silica gel column chromatography, and the obtained crude crystals were suspended in diisopropyl ether and collected by filtration to give the title compound (5.28 g) as white crystals.

Workup

  1. temperatureunder reflux for 8 hr
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. customthe obtained crude crystals
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f3d6551c4d49474d84b2f422e112127b
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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