Water → HCID 58368651, compound

HRID 1192547Notes

Reaction equation

HRID 1192547 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([Cl:17])=[CH:9][C:8]=1[C:18](=[O:20])[CH3:19])(=O)=O.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([F:23])[CH:29]=2)=[C:8]([C:18](=[O:20])[CH3:19])[CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 58368456HCID 58368456, compound

Product 1

HCID 58368651HCID 58368651, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-acetyl-4-chloro-1-naphthyl trifluoromethanesulfonate (0.100 g, 0.284 mmol, from Example 45, Step 2) and (3-fluorophenyl)boronic acid (0.048 g, 0.34 mmol) in 1,4-dioxane (1 mL) was added 1 N solution of sodium carbonate in water (0.43 mL, 0.43 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol). The mixture was heated at 100° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, and concentrated. The residue was purified on silica gel, eluting with 0 to 40% ethyl acetate in hexane, to give the desired product (56 mg, 66%). LCMS calculated for C18H13ClFO (M+H)+: m/z=299.1; Found: 299.0.

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel
  6. washeluting with 0 to 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5abcbf4ad69144ef99367a3f931e82b7
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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