N,N-Dimethylglycine → 5-(4-Fluorophenoxy)-2-methoxypyridine

HRID 1948273

반응식

HRID 1948273 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[F:10][C:11]1[CH:18]=[CH:17][C:14](CO)=[CH:13][CH:12]=1.CN(CC(O)=[O:24])C>O1CCOCC1.CN(C=O)C.[Cu]I>[F:10][C:11]1[CH:18]=[CH:17][C:14]([O:24][C:2]2[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 3

HCID 673N,N-DimethylglycineHCID 680224-Fluorobenzylic alcoholHCID 27348955-Bromo-2-methoxypyridine

생성물 1

HCID 442541925-(4-Fluorophenoxy)-2-methoxypyridine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

실험 절차

According to Scheme 32 Method A: 5-Bromo-2-methoxypyridine (5.32 mmol, 1.00 g), 4-fluorobenzylalcohol (7.98 mmol, 0.90 g), N,N-dimethylaminoacetic acid (15.9 mmol, 1.69 g), CuI (5.32 mmol, 1.01 g), CsCO3 (12.4 mmol, 4.05 g) in dioxane (25 mL) and DMF (2.5 mL) were heated at 150° C. for 25 min. under microwave irradiation conditions. Then the cooled crude reaction was filtered off over celite. The filtrate was washed with saturated aqueous NH4Cl solution and extracted with AcOEt. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge (heptane/AcOEt, 80/20). The product fractions were collected and the solvent was evaporated to give a mixture of the desired product contaminated with 4-fluorobenzylalcohol. This residue was taken up in AcOEt and washed with aqueous solution of NaOH 1N. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated under reduced pressure giving 5-(4-fluorophenoxy)-2-methoxypyridine (520 mg, 45%).

후처리

  1. temperatureThen the cooled crude
  2. customreaction
  3. filtrationwas filtered off over celite
  4. washThe filtrate was washed with saturated aqueous NH4Cl solution
  5. extractionextracted with AcOEt
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified in a manifold (vac.)
  10. customThe product fractions were collected
  11. customthe solvent was evaporated
  12. customto give

출처 및 근거

ORD 기록
ord-4dc56a6c36af44608627fc4010fe7b5a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

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