Potassium Carbonate → Methyl 6-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-pyridinecarboxylate

HRID 1717207ノート

反応式

HRID 1717207 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32]>CC(C)=O>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 136146660Methyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate

生成物 1

HCID 59468948Methyl 6-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-pyridinecarboxylate収率 73.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate (D80, 650 mg, 2.84 mmol) in acetone (8 ml) were added K2CO3 (780 mg, 5.67 mmol) and 1-(bromomethyl)-2-fluorobenzene (805 mg, 4.26 mmol). The mixture was stirred at 60° C. under nitrogen atmosphere for 6 h. Solvent was removed under reduced pressure and the residue was dissolved in AcOEt. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated to dryness. The crude compound was purified by flash chromatography on 25 g silica gel cartridge, using a gradient of cyclohexane/ethylacetate 10/0 to 8/2 as eluent, to give the title compound (700 mg, 73%).

後処理

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in AcOEt
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude compound was purified by flash chromatography on 25 g silica gel cartridge

出典と根拠

ORDレコード
ord-52b6a4dde2f64e4c97dbdfbf4df695a3
出典データセット
uspto-grants-2010_09
特許番号
US07803833B2

反応ノート

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