Pyridine → HCID 66777841、化合物

HRID 2090941ノート

反応式

HRID 2090941 の反応式
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:5][CH:6]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.N1C=CC=CC=1>CN(C)C(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([N:5]2[CH:6]=[C:2]([CH3:1])[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4]2)[CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 2734370(3-Methoxyphenyl)boronic acidHCID 178470484HCID 178470484、化合物

生成物 1

HCID 66777841HCID 66777841、化合物収率 46%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 31374Dimethylacetamide溶媒

実験手順

Ethyl 4-methyl-1H-pyrazole-3-carboxylate (2.58 g) was dissolved in N,N-dimethylacetamide (50 mL), 3-methoxyphenylboronic acid (5.0 g), copper acetate (6.0 g) and pyridine (5.3 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL) was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (1.9 g, 46%) as a pale-yellow oil.

後処理

  1. filtrationThe reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL)
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

出典と根拠

ORDレコード
ord-fa0a122f1f5f4a1d99bbf85b53cc5e93
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

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