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

HRID 41968

反応式

HRID 41968 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7604022984de470db2eaaeb7e6b15206
出典データセット
uspto-grants-2013_09
特許番号
US08536172B2

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