2-Aminopyridine → Methyl 2-(2-pyridylamino)isonicotinate

HRID 452633

반응식

HRID 452633 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

8

반응물 3

HCID 104392-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 2736842Methyl 2-chloropyridine-4-carboxylate

생성물 1

HCID 68664232Methyl 2-(2-pyridylamino)isonicotinate수율 65%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of methyl 2-chloroisonicotinate (1.00 g, 5.83 mmol), 2-aminopyridine (658 mg, 6.99 mmol), tris(dibenzylideneacetone)dipalladium(0) (107 mg, 0.17 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (139 mg, 0.29 mmol) and tripotassium phosphate (3.09 g, 14.6 mmol) in toluene (30 mL) was heated under reflux under an argon atmosphere overnight. After cooling, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=9/1-2/3) and recrystallized from hexane/ethyl acetate to give the title compound (866 mg, yield 65%) as colorless crystals.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux under an argon atmosphere overnight
  3. temperatureAfter cooling
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=9/1-2/3)
  8. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-5947a725ed7340a889cf8a5963cb710d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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