Potassium Carbonate → HCID 9905800, compound

HRID 1797183Notes

Reaction equation

HRID 1797183 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].[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.O>O>[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=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 11430Potassium CarbonateHCID 2762745Pyridine-2-boronic acidHCID 9800265[2-Fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amineHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 9905800HCID 9905800, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Scheme VI, Step A′: [2-fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amine (200 mg, 0.52 mmol, prepared in example 1), pyridyl boronic acid (93 mg, 0.76 mmol), potassium carbonate (104 mg, 0.76 mmol), tetrakis(triphenyl phosphine)palladium(0) (41 mg, 0.036 mmol), and dioxane/water (20 mL, 3:1) were mixed together in a 100 mL single neck flask and stirred at 90° C. over night. In the morning, the reaction was cooled to room temperature and poured into H2O, and the desired product was extracted with ethyl acetate. The organic layer was backwashed once with H2O, dried over K2CO3, filtered, and concentrated under reduced pressure to yield 235 mg. of a viscous oil. This material was purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 1:1 to yield the title compound (126 mg, 72%) as a semi-solid. Ion spray M.S. 337.2 (M*+1).

Workup

  1. temperatureIn the morning, the reaction was cooled to room temperature
  2. extractionthe desired product was extracted with ethyl acetate
  3. dry with materialdried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield 235 mg
  7. customThis material was purified via silica gel chromatography
  8. washwhile eluting with a solvent of methylene chloride/ethyl acetate 1:1

Sources & evidence

ORD record
ord-76cb46b7a86044439e61d20f658381b5
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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