Pyridine → HCID 59598367, compound

HRID 2359710Notes

Reaction equation

HRID 2359710 reaction equation
[OH:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]([I:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ClC(Cl)C.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[I:12][C:8]1[CH:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2](=[O:1])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 1049PyridineHCID 63651,1-DichloroethaneHCID 66827Phenylboronic AcidHCID 178498694HCID 178498694, compound

Product 1

HCID 59598367HCID 59598367, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

Methyl 2-hydroxy-4-iodonicotinate (123 mg, 441 μmol), phenylboronic acid (161 mg, 1322 μmol), copper acetate (160 mg, 882 μmol) were combined. Dichloroethane (6 mL) was added followed by molecular sieves 4 Å activated (490 mg) and pyridine (143 μl, 1763 μmol). The reaction mixture was stirred at 55° C. for 3 h. LCMS analysis of an aliquot showed the reaction was complete. The reaction mixture was diluted with dichloromethane and filtered through a pad of celite (rinsing with dichloromethane). The filtrate was concentrated in vacuo and purification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 97.5/2.5) afforded methyl 4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate (142 mg, 400 μmol, 91% yield). MS (ESI pos. ion) m/z: 356 (MH+). Calc'd exact mass for C13H10INO3: 355.

Workup

  1. filtrationfiltered through a pad of celite (rinsing with dichloromethane)
  2. concentrationThe filtrate was concentrated in vacuo and purification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 97.5/2.5)

Sources & evidence

ORD record
ord-66297e7aeaa841608515dfc6b07e8e57
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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