Sodium hydride → 1-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropane-1-carbonitrile

HRID 2090412

反応式

HRID 2090412 の反応式
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.CS(O[CH2:20][C:21]1([C:24]#[N:25])[CH2:23][CH2:22]1)(=O)=O.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:20][C:21]3([C:24]#[N:25])[CH2:23][CH2:22]3)[CH:10]=2)[O:3]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 54220629HCID 54220629、化合物

生成物 1

HCID 684695851-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropane-1-carbonitrile収率 109.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.1 g, 0.5 mmol), (1-cyanocyclopropyl)methyl methanesulfonate (0.14 g, 0.77 mmol), and sodium hydride (31 mg, 0.77 mmol) in N,N-dimethylformamide (1 mL) was stirred at 110° C. for 2 h. After cooling, it was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4. After filtration the filtrate was concentrated to yield 0.15 g of the crude product which was used in the next step reaction without further purification.

後処理

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

出典と根拠

ORDレコード
ord-ed15accddbac4efcbc3aea14e828cd46
出典データセット
uspto-grants-2013_05
特許番号
US08436008B2

関連ノート

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