Water → Methyl 3-amino-6-chloro-2-methylisonicotinate

HRID 887704노트

반응식

HRID 887704 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6](Br)[C:5]=1[NH2:12].[C:14](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([CH3:14])[C:5]=1[NH2:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59355453Methyl 3-amino-2-bromo-6-chloro-4-pyridinecarboxylate

생성물 1

HCID 59355376Methyl 3-amino-6-chloro-2-methylisonicotinate수율 26.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (500 mg), potassium carbonate (829 mg), tetrakis(triphenyl phosphine)palladium(0) and trimethylboroxine (276 mg) were suspended in dioxane (15 mL). Water (1.5 mL) was added and the mixture was degassed using subsequent evaporation and flushing with nitrogen (5×). The reaction mixture was stirred under reflux for 7 hours. After cooling to room temperature, the mixture was quenched with water and extracted 2× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25) to afford 100 mg of the title compound of the formula

후처리

  1. customthe mixture was degassed
  2. customevaporation
  3. customflushing with nitrogen (5×)
  4. temperatureunder reflux for 7 hours
  5. customthe mixture was quenched with water
  6. extractionextracted 2× with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuum
  10. customThe residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25)

출처 및 근거

ORD 기록
ord-fdd725c27c344041857b94a3b8c3062d
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247431B2

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