Water → methyl 2-[(E)-2-phenylvinyl]isonicotinate

HRID 383916노트

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HRID 383916 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]1(/[CH:18]=[CH:19]/OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]1(/[CH:18]=[CH:19]/[C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 22100376[(E)-2-phenylvinyl]boric acid

생성물 1

HCID 59291512methyl 2-[(E)-2-phenylvinyl]isonicotinate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a mixture of methyl 2-chloroisonicotinate, Pd(PPh3)4, and [(E)-2-phenylvinyl]boric acid in dioxane was added a 2 M aqueous Na2CO3 solution, followed by stirring at 90° C. for 5 hours. To the reaction mixture was added water, and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, and the filtrate was then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain methyl 2-[(E)-2-phenylvinyl]isonicotinate as a pale yellow solid.

후처리

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc)

출처 및 근거

ORD 기록
ord-1b46bf55431b4ccda8eb1e1090edfe2f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367696B2

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