2-Fluorobenzoyl chloride → HCID 18930608, compound

HRID 1598908Notes

Reaction equation

HRID 1598908 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([Sn](CCCC)(CCCC)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:36])[CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])CCC.[F-].[K+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:36])[CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])=[O:5]

Participants

5

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 522689Potassium FluorideHCID 18930537HCID 18930537, compound

Product 1

HCID 18930608HCID 18930608, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 2-fluorobenzoylchloride (208 μl, 1.74 mmol) in chloroform (20 ml) is added at room temperature dichlorobisacetonitrile palladium (15 mg, 0.044 mmol). Then, a solution of N-(2-tributylstannylphenyl)-2-(benzyloxycarbonylamino)acetamide (1 g, 1.74 mmol) in chloroform (3 ml) is added and stirred at 50° C. for 35 minutes. Dichlorobisacetonitrile palladium (15 mg, 0.044 mmol) is added and the stirring continued for another 10 minutes. After allowing to cool, an aqueous solution of 50% potassium fluoride is added to the reaction mixture and stirred for 30 minutes. The precipitate is removed by filteration. After this procedure is repeated once more, the organic layer is washed with saturated saline, dried over anhydrous magnesium sulfate, and then concentrated. The residue is purified by silica gel column chromatography to obtain the objective compound (570 mg). Yield 80%.

Workup

  1. waitthe stirring continued for another 10 minutes
  2. temperatureto cool
  3. stirringstirred for 30 minutes
  4. customThe precipitate is removed by filteration
  5. washthe organic layer is washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d952768b2104dba8504551fabf77d6b
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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