Potassium Carbonate → Methyl 3-(3-pyridinyl)benzoate

HRID 880253노트

반응식

HRID 880253 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:16]=[N:17][CH:18]=[CH:19][CH:20]=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:17]1[CH:18]=[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]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

생성물 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoate수율 90%

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), 3-bromopyridine (479 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 minutes with microwave heating under N2. The catalyst was then filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the desired product and used directly in the next step. (630 mg Yield 90%).

후처리

  1. temperaturewith microwave heating under N2
  2. filtrationThe catalyst was then filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography

출처 및 근거

ORD 기록
ord-1847187d0eac452281a98d3d17245484
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993555B2

반응 노트

불러오는 중…