Picolinic acid → HCID 70654373, compound

HRID 539494Notes

Reaction equation

HRID 539494 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](O)=O.[OH2:24].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.CS(C)=O>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][C:4]1[CH:3]=[C:2]([CH:14]=[CH:13][CH:12]=1)[O:24][C:2]1[CH:14]=[CH:13][C:18]2[C:17]3[CH:10]=[CH:9][CH:8]=[CH:21][C:16]=3[N:15]3[CH:11]=[CH:6][N:7]=[C:20]3[C:19]=2[CH:3]=1

Participants

6

Reactant 3

HCID 1018Picolinic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 53953865HCID 53953865, compound

Product 1

HCID 70654373HCID 70654373, compoundYield 135%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

2-(3-Iodophenoxy)pyridine (0.634 g, 2.13 mmol), imidazo[1,2-]phenanthridin-11-ol (0.5 g, 2.13 mmol), copper(I) iodide (0.122 g, 0.640 mmol), picolinic acid (0.394 g, 3.20 mmol) and potassium phosphate monohydrate (1.72 g, 7.47 mmol) were added to 70 mL DMSO and degassed for 30 minutes with bubbling nitrogen gas. The reaction mixture was heated to 100° C. for 24 h, cooled to room temperature and poured over 100 mL water. The organic materials were extracted with ethyl acetate (3×50 mL) and the combined extracts washed with 1N NaOH (1×50 mL) and saturated ammonium chloride solution (1×50 mL), dried over sodium sulfate and the solvents were removed under reduced pressure. The crude material was purified by column chromatography over silica gel using ethyl acetate/hexanes as eluent to give 11-(3-(pyridin-2-yloxy)phenoxy)imidazo[1,2-f]phenanthridine (0.58 g, 67%) was isolated as a white solid.

Workup

  1. customdegassed for 30 minutes with bubbling nitrogen gas
  2. temperaturecooled to room temperature
  3. additionpoured over 100 mL water
  4. extractionThe organic materials were extracted with ethyl acetate (3×50 mL)
  5. washthe combined extracts washed with 1N NaOH (1×50 mL) and saturated ammonium chloride solution (1×50 mL)
  6. dry with materialdried over sodium sulfate
  7. customthe solvents were removed under reduced pressure
  8. customThe crude material was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-995693cda54a409ea9625b88fec7ea43
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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