Water → HCID 9862554, compound

HRID 1797175Notes

Reaction equation

HRID 1797175 reaction equation
[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[C:19]1(OB(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.O>[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 9800265[2-Fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amine

Product 1

HCID 9862554HCID 9862554, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

Scheme VI, Step A′: Into a 10 mL single neck flask was placed [2-fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amine (113 mg, 0.29 mmol, prepared in example 1), phenyl boric acid (54 mg, 0.44 mmol), potassium carbonate (61 mg, 0.44 mmol), and tetrakis(triphenyl phosphine)Pd(0) (17 mg, 0.02 mmol) in a mixture of dioxane/water (3:1, 7 mL). The mixture was then heated at 100° C. with stirring for 18 hours. The reaction was then cooled to room temperature and poured into H2O. The mixture was extracted with EtOAc and the organic layer was washed twice with H2O, dried over anhydrous Na2SO4, filtered, and concentrated under reduced vacuum. The resulting semi-solid was purified via radial chromatography (Chromatotron, Harrison Research Inc., 840 Moana Court, Palo Alto, Calif. 94306) using a 2000 micron rotor (silica gel) and eluting with a solvent of Hexane/EtOAc 4:1 to provide the title compound (33 mg, 34%) as a slowly crystallizing tan oil. Ion spray M.S. 335 (M*+1).

Workup

  1. customScheme VI, Step A′: Into a 10 mL single neck flask was placed
  2. temperatureThe reaction was then cooled to room temperature
  3. extractionThe mixture was extracted with EtOAc
  4. washthe organic layer was washed twice with H2O
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced vacuum
  8. customThe resulting semi-solid was purified via radial chromatography (Chromatotron, Harrison Research Inc., 840 Moana Court, Palo Alto, Calif. 94306)
  9. washeluting with a solvent of Hexane/EtOAc 4:1

Sources & evidence

ORD record
ord-2aa30d5d3bad437d822b17469d831bf5
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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