Hydrochloric Acid → Ethyl 5-bromo-2-ethoxy-6-(4-fluorophenyl)nicotinate

HRID 531033노트

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HRID 531033 반응식
[OH-:1].[K+].[Br:3][C:4]1[C:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:6][C:7]([O:12][CH2:13][CH3:14])=[C:8]([CH:11]=1)[C:9]#N.C1C[O:25][CH2:24][CH2:23]1.Cl>C(O)C>[Br:3][C:4]1[C:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:6][C:7]([O:12][CH2:13][CH3:14])=[C:8]([CH:11]=1)[C:9]([O:25][CH2:24][CH3:23])=[O:1]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 1179921125-Bromo-2-ethoxy-6-(4-fluorophenyl)nicotinonitrile

생성물 1

HCID 90424072Ethyl 5-bromo-2-ethoxy-6-(4-fluorophenyl)nicotinate

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

An 8 M aqueous potassium hydroxide solution (14.6 mL) was added to a mixture of 5-bromo-2-ethoxy-6-(4-fluorophenyl)nicotinonitrile (3.75 g), THF (10 mL), and ethanol (10 mL), and the resultant mixture was stirred overnight at 100° C. The reaction mixture was neutralized with 6 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. Potassium carbonate (3.23 g) and iodoethane (1.40 mL) were added to a mixture of the obtained residue and DMF (10 mL), and the resultant mixture was stirred at 60° C. for 30 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.40 g).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionPotassium carbonate (3.23 g) and iodoethane (1.40 mL) were added to a mixture of the obtained residue and DMF (10 mL)
  5. additionWater was added to the reaction mixture
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5c20242c8fc94c4285971dbb8d63b014
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353108B2

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