Potassium Carbonate → HCID 22176548, compound

HRID 1797205Notes

Reaction equation

HRID 1797205 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([NH:6][CH2:7][C:8]([F:17])([C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1)[CH3:9])(=[O:5])=[O:4].[NH2:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.O>O>[NH2:19][C:20]1[CH:25]=[C:24]([C:13]2[CH:14]=[CH:15][C:10]([C:8]([F:17])([CH3:9])[CH2:7][NH:6][S:3]([N:2]([CH3:18])[CH3:1])(=[O:5])=[O:4])=[CH:11][CH:12]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 218864351,4-Dioxane--water (1/1)HCID 22176551HCID 22176551, compound

Product 1

HCID 22176548HCID 22176548, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

[(Dimethylamino)sulfonyl][2-fluoro-2-(4-iodophenyl)propyl]amine (386, 1.0 mmol, prepared in example 36), 3-aminobenzeneboronic acid (201 mg, 1.3 mmol), potassium carbonate (179 mg, 1.3 mmol), tetrakis(triphenyl phosphine)palladium(0) (58 mg, 0.05 mmol), and dioxane/water (60 mL, 3:1) are mixed together in a 100 mL single neck flask and stirred at 70° C. over night. In the morning, the reaction is cooled to room temperature and poured into H2O, and the desired product is extracted with ethyl acetate. The organic layer is backwashed once with H2O, dried over K2CO3, filtered, and concentrated under reduced pressure. The crude material is purified via silica gel chromatography employing the Chromatotron and using a 2000 micron rotor with hexane/ethyl acetate eluent to provide the title compound.

Workup

  1. temperatureIn the morning, the reaction is cooled to room temperature
  2. extractionthe desired product is extracted with ethyl acetate
  3. dry with materialdried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material is purified via silica gel chromatography

Sources & evidence

ORD record
ord-8844839cd5f54fafbbff53f1e4eb4cde
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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