Dimethylformamide → HCID 67168187、化合物

HRID 1517598ノート

反応式

HRID 1517598 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:11])=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].FN1C=C[CH:22]=[CH:21][CH:20]1[Br:25].[CH3:26][N:27]([CH3:30])C=O>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:11])=[N:8][N:9]([C:26]2[C:20]([Br:25])=[CH:21][CH:22]=[CH:30][N:27]=2)[CH:10]=1)=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86653545HCID 86653545、化合物HCID 178469911HCID 178469911、化合物

生成物 1

HCID 67168187HCID 67168187、化合物収率 79%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

To the solution of 3-methyl-pyrazole-4-carboxylic acid ethyl ester (2.0 g, 13 mmol) in dry dimethylformamide (30 mL) is added potassium carbonate (7.2 g, 52 mmol) at room temperature. The reaction mixture is stirred at 40° C. for 30 min and then 1-fluoro-2-bromopyridine (3.0 g, 17 mmol) is added. The reaction mixture is stirred at 70° C. for 4 h. The reaction mixture is cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture was purified by chromatography on silica gel eluting with hexane/ethyl acetate (85:15, 80:20) to yield 3.2 g (79%) of 1-(3-bromo-pyridin-2-yl)-3-methyl-pyrazole-4-carboxylic acid ethyl ester. MS (m/z): 312 (M+3), 310 (M+1).

後処理

  1. stirringThe reaction mixture is stirred at 70° C. for 4 h
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by chromatography on silica gel eluting with hexane/ethyl acetate (85:15, 80:20)

出典と根拠

ORDレコード
ord-d0962d93824942bd937f7316ba1af960
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

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