Potassium Carbonate → HCID 54705574, compound

HRID 1785823Notes

Reaction equation

HRID 1785823 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.[Cu]I>[OH:19][C:17]1[CH:16]=[CH:15][N:14]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[C:13](=[O:12])[CH:18]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 69273Methyl 4-iodobenzoateHCID 178516518HCID 178516518, compound

Product 1

HCID 54705574HCID 54705574, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 4-iodobenzoate (0.421 g, 1.6 mmol), 2,4-dihydroxypyridine (0.174 g, 1.34 mmol), CuI (25 mg, 0.134 mmol) and K2CO3 (200 mg) in DMF (2 mL) was heated to 150° C. in a sealed vial for 4 hours, diluted with ethyl acetate (100 mL), washed with water (30 mL) and brine (30 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate to provide the desired product. MS (APCI) m/e 246 (M+H)+.

Workup

  1. washwashed with water (30 mL) and brine (30 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-43950974ca274bdf8bd456ba47b3e21b
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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