Potassium Carbonate → HCID 18472341、化合物

HRID 1277203ノート

反応式

HRID 1277203 の反応式
[CH3:1][N:2]([O:12][CH3:13])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1)=[O:4].B([O-])([O-])O[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.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>[CH3:1][N:2]([O:12][CH3:13])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:10]=1)=[O:4]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 866453334-Methylphenyl borate

生成物 1

HCID 18472341HCID 18472341、化合物収率 102.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 66602552Toluene-ethanol water溶媒

実験手順

Under argon atmosphere, a solution of N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (3.70 g), 4-methyl-phenyl borate (2.26 g) and potassium carbonate (4.17 g) in toluene-ethanol-water (100-10-10 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.52 g), and the mixture was refluxed for 16 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:2→1:1) to give N-methyl-N-methoxy-5-(4-methylphenyl)pyridine-3-carboxamide (3.97 g) as yellow oil.

後処理

  1. temperaturethe mixture was refluxed for 16 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:2→1:1)

出典と根拠

ORDレコード
ord-c397168a1d31463b85c383828ac35d8e
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

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