Potassium Carbonate → Methyl 3-(4-pyridyl)benzoate

HRID 880256노트

반응식

HRID 880256 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:18]1[CH:19]=[CH:20][C:15]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

생성물 1

HCID 5152687Methyl 3-(4-pyridyl)benzoate수율 98.5%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (600 mg, 3.33 mmol), 4-bromopyridine (583.5 mg, 3.0 mmol), K2CO3 (1.2 g, 9.0 mmol) and Pd(dppf)Cl2 (50 mg) in a solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 min with microwave heating. The catalyst was filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the title product (630 mg Yield 90%).

후처리

  1. temperatureheating
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography

출처 및 근거

ORD 기록
ord-0d5b609796d5498da36237ae9c0f9c11
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993555B2

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