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

HRID 1948273

反応式

HRID 1948273 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4dc56a6c36af44608627fc4010fe7b5a
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

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