Cesium fluoride → HCID 17966030, compound

HRID 2253319Notes

Reaction equation

HRID 2253319 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.[F-].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([C:2]2[C:9]([CH3:10])=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 888943-Chloro-p-toluonitrileHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 17966030HCID 17966030, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-chloro-4-methylbenzonitrile (3.30 g, 20 mmol), 3-methoxyphenylboronic acid (4.56 g, 30 mmol), palladium acetate (89.8 mg, 0.4 mmol), 2-dicyclohexylphosphanyl-2′-dimethylaminobiphenyl (0.236 g, 0.6 mmol), and CsF (9.11 g, 60 mmol) in dioxane (60 mL) at room temperature was stirred for 12 hours, and concentrated. The concentrate was dissolved in ethyl acetate (10 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexane to provide 4.38 g (98%) of the desired product. MS (DCI/NH3) m/z 241 (M+NH4)+; 1H NMR (CDCl3) δ 7.55-7.52 (m, 2H), 7.38-7.33 (m, 2H), 6.94 (m, 1H), 6.86 (m, 1H), 6.80 (m, 1H), 3.84 (s, 3H), 2.32 (s, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in ethyl acetate (10 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexane

Sources & evidence

ORD record
ord-436ab2b196254d5199e3eb9b04618f38
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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