Cyanogen Bromide → 4-[2-(4-Methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-carbonitrile

HRID 42145노트

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HRID 42145 반응식
[CH3:1][S:2]([C:5]1[CH:24]=[CH:23][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])O.[Na+].[N:30]#[C:31]Br>ClCCl.O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:31]#[N:30])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:23][CH:24]=1)(=[O:3])=[O:4]

참가 물질

6

반응물 3

HCID 10476Cyanogen BromideHCID 516892Sodium Bicarbonate2회HCID 670831594-[2-(4-Methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine

생성물 1

HCID 866542604-[2-(4-Methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-carbonitrile수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine (124 mg, 0.358 mmol) in dichloromethane (1 mL) was added a solution of sodium hydrogen carbonate (60 mg, 0.716 mmol) in water (0.5 mL). The mixture was cooled in an ice bath followed by the addition of a solution of cyanogen bromide (45 mg, 0.430 mmol) in dichloromethane (1 mL). The mixture was stirred at 0° C. for 30 minutes and then stirred at room temperature for an additional 1 hour. The mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (114 mg, yield 86%).

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringstirred at room temperature for an additional 1 hour
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-cf10702caf9c415fbe8aacbc35050d46
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536176B2

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