1-Methylimidazole → HCID 67461331, compound

HRID 1049959Notes

Reaction equation

HRID 1049959 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])N=1.[CH3:23]N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.C1(C)C=CC=CC=1>[Br:22][C:18]1[CH:23]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 204557773-(2-Pyridinyloxy)phenol

Product 1

HCID 67461331HCID 67461331, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Under a nitrogen atmosphere, a pressure vessel was charged with a magnetic stir bar, 3-(pyridin-2-yloxy)phenol (50 mmol), 2,6-dibromopyridine (50 mmol), 1-methylimidazole (25 mmol), and potassium carbonate (100 mmol). Toluene (80 mL) was added and bubbled with nitrogen for 20 minutes before copper(I) iodide (5 mmol) was added and the solution bubbled for 10 minutes further. The vessel was sealed and heated to 140° C. while stirring. After 2 days, the solution was allowed to cool and the solids were filtered off and rinsed with dichloromethane. The filtrate was added to a separatory funnel containing DCM and water. The water phase was washed 3 times with 75 mL DCM, and the combined organic layers were washed once with pure water. The organic layer was collected, dried with magnesium sulfate, filtered, and the filtrate reduced by rotary evaporation. The resulting oil was purified by column chromatography using DCM over silica resulting in the pure product 2-(3-(3-bromophenoxy)phenoxy)pyridine with a 60% yield. 1H NMR (CDCl3): 6.80-6.85 (m, 2H), 6.91 (s, 1H), 6.94 (s, 1H), 6.97-7.03 (m, 2H), 7.19 (vt, 1H), 7.21-7.24 (m, 2H), 7.36 (vt, 1H), 7.70 (dd, 1H), 8.21 (dd, 1H).

Workup

  1. additionUnder a nitrogen atmosphere, a pressure vessel was charged with a magnetic stir bar
  2. additionwas added
  3. customthe solution bubbled for 10 minutes further
  4. customThe vessel was sealed
  5. temperatureto cool
  6. filtrationthe solids were filtered off
  7. washrinsed with dichloromethane
  8. additionThe filtrate was added to a separatory funnel
  9. additioncontaining DCM and water
  10. washThe water phase was washed 3 times with 75 mL DCM
  11. washthe combined organic layers were washed once with pure water
  12. customThe organic layer was collected
  13. dry with materialdried with magnesium sulfate
  14. filtrationfiltered
  15. customthe filtrate reduced by rotary evaporation
  16. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-7b443aae565442a5b3118d291e73c57d
Source dataset
uspto-grants-2016_07
Patent number
US09382273B2

Reaction notes

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