Cesium carbonate → 6-(3-Methoxyphenyl)-2-naphthalenecarbonitrile

HRID 1384183Notes

Reaction equation

HRID 1384183 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17]#[N:18])[CH:11]=[CH:10]2)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:27][O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:27][O:28][C:29]1[CH:34]=[C:33]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([C:17]#[N:18])[CH:11]=[CH:10]3)[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 155418226-Cyano-2-naphthyl trifluoromethanesulfonate

Product 1

HCID 217068506-(3-Methoxyphenyl)-2-naphthalenecarbonitrileYield 54%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Example 28B (300 mg, 1 mmol), palladium (II) acetate (22 mg, 0.1 mmol) and 1-1′-bis(diphenyphosphino)ferrocene (111 mg, 0.2 mmol) was stirred in DMF (3 mL) for 15 min, treated with Cs2CO3 (813 mg, 2.5 mmol) and 3-methoxyphenylboronic acid (228 mg, 1.5 mmol), stirred for 20 min at 80° C., cooled, treated with pH 7 buffer (10 mL) and extracted with diethyl ether. The ether extracts were dried (MgSO4), concentrated and purified on silica gel with 10% ethyl acetate/hexane to provide 140 mg of the title compound as a white solid.

Workup

  1. temperaturecooled
  2. additiontreated with pH 7 buffer (10 mL)
  3. extractionextracted with diethyl ether
  4. dry with materialThe ether extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified on silica gel with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-12881a0ffcdb43c1a9416125b7b4f7a2
Source dataset
uspto-grants-2001_07
Patent number
US06258822B1

Reaction notes

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