Tetrabutylammonium Fluoride → 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine

HRID 1515833ノート

反応式

HRID 1515833 の反応式
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:22]([CH3:24])[CH3:23])(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:19][C:17]1[CH:18]=[C:13]2[CH:12]=[C:11]([C:20]([C:25]3[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][CH:30]=3)=[CH:21][CH:22]([CH3:24])[CH3:23])[NH:10][C:14]2=[N:15][CH:16]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 672291491-benzenesulfonyl-5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 672297395-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A mixture of 1-benzenesulfonyl-5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (900 mg, 1.8 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 4 ml) was stirred at 25° C. for 20 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (30 mL). The mixture was extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×25 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (600 mg, 92%): LC/MS m/e calcd for C19H19FN2O2S [M+H]+ 359.44, observed 358.8.

後処理

  1. customThe reaction was quenched with a saturated aqueous ammonium chloride solution (30 mL)
  2. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  3. washwashed with a saturated aqueous ammonium chloride solution (3×25 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-635b2b3c9d974c98b08848081cd07715
出典データセット
uspto-grants-2012_07
特許番号
US08222416B2

反応ノート

読み込み中…