Diisopropylethylamine → 2-Fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde

HRID 41968

반응식

HRID 41968 반응식
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].Cl.[CH3:12][S:13]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].CCN(C(C)C)C(C)C>C(#N)C>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([N:19]2[CH2:20][CH2:21][CH:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH2:17][CH2:18]2)[C:3]=1[CH:4]=[O:5]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1362842,6-DifluorobenzaldehydeHCID 230616984-Methanesulfonylpiperidine hydrochloride

생성물 1

HCID 581379622-Fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde수율 84%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

In a 250 mL round bottom flask, 2,6-difluorobenzaldehyde (7.12 g, 5.4 mL, 50.1 mmol), 4-methanesulfonylpiperidine hydrochloride (10 g, 50.1 mmol) and DIPEA (7.77 g, 60.1 mmol) were combined with acetonitrile (75 mL). The mixture was stirred and heated at 80° C. overnight. The mixture was evaporated and extracted with dichloromethane and citric acid solution. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The crude solid was triturated with cold ethyl acetate to afford 2-fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde (12 g, 84% yield). LC-MS calcd for C13H16FNO3S (m/e) 285.08, obsd 286.0 (M+H).

후처리

  1. customThe mixture was evaporated
  2. extractionextracted with dichloromethane and citric acid solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude solid was triturated with cold ethyl acetate

출처 및 근거

ORD 기록
ord-7604022984de470db2eaaeb7e6b15206
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536172B2

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