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

HRID 2244354ノート

反応式

HRID 2244354 の反応式
[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]

参加物

7

反応物 3

HCID 81998Tributylvinyltin2 回HCID 433294Lithium ChlorideHCID 687024045-Bromo-2-methylamino-nicotinic acid ethyl ester

生成物 1

HCID 686973712-Methylamino-5-vinyl-nicotinic acid ethyl ester収率 91%

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4cf46e7d474e49d5a06558f9b773212e
出典データセット
uspto-grants-2010_03
特許番号
US07678818B2

反応ノート

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