Pyridine → HCID 59191277, compound

HRID 1023943Notes

Reaction equation

HRID 1023943 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][O:15][C:16]1[CH:21]=[C:20]([CH2:22][CH3:23])[CH:19]=[CH:18][C:17]=1[OH:24].C(N(CC)CC)C.N1C=CC=CC=1>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:24][C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH3:23])=[CH:21][C:16]=2[O:15][CH3:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 624654-EthylguaiacolHCID 27343644-(Methanesulfonyl)phenylboronic acid

Product 1

HCID 59191277HCID 59191277, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of Cu(OAc)2 (3.0 mmol; 543 mg), 4-(methanesulphonyl)benzeneboronic acid (4.0 mmol; 800 mg) and activated molecular sieves (800 mg) under air, in anhydrous dichloromethane (5 mL), were added 2-methoxy-4-ethylphenol (2.0 mmol; 0.28 mL), anhydrous triethylamine (10 mmol; 1.4 mL), and anhydrous pyridine (10 mmol; 0.8 mL). The reaction was stirred for 2 days at room temperature. The crude was filtered on silica gel, washed with ethyl acetate, concentrated. The residue was then purified by column chromatography (gradient cyclohexane/dichloromethane) to yield the title compound as clear oil (617 mg; 2.0 mmol; quantitative).

Workup

  1. filtrationThe crude was filtered on silica gel
  2. washwashed with ethyl acetate
  3. concentrationconcentrated
  4. customThe residue was then purified by column chromatography (gradient cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-4f46db6710644972979bfe4314b0c579
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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