Dimethylformamide → HCID 67168187, 화합물

HRID 1517598노트

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HRID 1517598 반응식
[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]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86653545HCID 86653545, 화합물HCID 178469911HCID 178469911, 화합물

생성물 1

HCID 67168187HCID 67168187, 화합물수율 79%

시약·촉매·용매 1

HCID 962Water용매

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온도
40 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d0962d93824942bd937f7316ba1af960
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

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