Methyl iodide → 1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 450453ノート

反応式

HRID 450453 の反応式
[CH3:1][C:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[CH:5][NH:4][N:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.CCOC(C)=O>[CH3:16][N:4]1[CH:5]=[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)[C:2]([CH3:1])=[N:3]1.[CH3:16][N:3]1[C:2]([CH3:1])=[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)[CH:5]=[N:4]1

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178434487HCID 178434487、化合物

生成物 2

HCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole収率 166.7%HCID 426473161,3-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.3 g, 1.442 mmol) and potassium carbonate (0.996 g, 7.21 mmol) were suspended in acetonitrile (10 ml) and stirred overnight at RT. Additional iodomethane (0.5 ml) was added and the mixture was stirred overnight at RT. The mixture was diluted with EtOAc and the inorganic salts were removed by filtration. The filtrate was evaporated to yield an inseparable mixture (2:1) of 1,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.267 g, 83% yield). MS (ESI) m/z: 223.1 (M+H+).

後処理

  1. stirringthe mixture was stirred overnight at RT
  2. customthe inorganic salts were removed by filtration
  3. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-58b83968c1d144188f08b04f53ea63ca
出典データセット
uspto-grants-2013_07
特許番号
US08486951B2

反応ノート

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