Tributylvinyltin → 2-Methylamino-5-vinyl-nicotinic acid ethyl ester

HRID 2244354노트

반응식

HRID 2244354 반응식
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2].[Cl-].[Li+].[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18]>CS(C)=O.[Cu]Cl.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>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([CH:17]=[CH2:18])[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2]

참가 물질

7

반응물 3

HCID 81998Tributylvinyltin2회HCID 433294Lithium ChlorideHCID 687024045-Bromo-2-methylamino-nicotinic acid ethyl ester

생성물 1

HCID 686973712-Methylamino-5-vinyl-nicotinic acid ethyl ester수율 91%

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 5-bromo-2-methylamino-nicotinic acid ethyl ester (100 mg, 0.39 mmol), lithium chloride (98 mg, 2.32 mmol), copper(I)chloride (191 mg, 1.93 mmol), vinyl tributyl tin (151 mg, 0.46 mmol), and tetrakis(triphenylphosphine)palladium(0) (45 mg, 39 μmol) in methyl sulfoxide (3.1 mL) was stirred at 65° C., then after 4 h another portion of vinyl tributyl tin (141 mg, 0.46 mmol) was added, and stirring was continued for 18 h. After cooling, the reaction mixture was partitioned between sat. aq. ammonium chloride solution and diethyl ether, the organic layer was washed with water, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (72 mg, 91%). Yellow liquid, MS (ISP): 207.1 (M+H)+.

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between sat. aq. ammonium chloride solution and diethyl ether
  3. washthe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-4cf46e7d474e49d5a06558f9b773212e
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678818B2

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