Water → HCID 86642503, compound

HRID 629608Notes

Reaction equation

HRID 629608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([O-:14])([O-])=O.[K+].[K+].[OH2:17]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:2]2[CH2:7][CH2:6][CH:5]([OH:17])[CH2:4][C:3]=2[CH:11]=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

Product 1

HCID 86642503HCID 86642503, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-chlorophenylboronic acid (6.88 g), EXAMPLE 224A (4.65 g), palladium(II) acetate (131 mg), K2CO3 (18.24 g) and tetrabutylammonium bromide (14.18 g) was added water (200 mL). The mixture was stirred at 50° C. for 4 hours, cooled, and diluted with ethyl acetate (400 mL) and washed with water (3×) and brine and dried over Na2SO4. After filtration and concentration, the residue was loaded on a column and eluted with 5-20% ethyl acetate in hexane to give the title compound.

Workup

  1. temperaturecooled
  2. washwashed with water (3×) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. washeluted with 5-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-23e166c1c08d48ac96563c34d8093ff0
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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