Tetrabutylammonium Fluoride → 2-bromo-5H-pyrrolo[2,3-b]pyrazine

HRID 272046ノート

反応式

HRID 272046 の反応式
[Br:1][C:2]1[N:3]=[C:4]([C:12]#[C:13][Si](C)(C)C)[C:5]([NH:8]C(=O)C)=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:13][NH:8][C:5]2=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 59836029N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide

生成物 1

HCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine収率 43.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of N-(5-Bromo-3-trimethylsilanylethynyl-pyrazin-2-yl)-acetamide (474 mg, 1.52 mmol) in THF (4 ml) was added dropwise a 1 M solution of tetra-n-butyl ammonium fluoride in THF (3.3 ml, 3.3 mmol). After stirring at reflux for 15 hours, the reaction mixture was concentrated in vacuum and water added. The aqueous layer was extracted three times with dichloromethane and the combined extracts were directly adsorbed on silica gel. Purification by silica gel chromatography with a gradient of ethyl acetate/hexanes afforded the title compound (130 mg, 43% yield) as a yellow solid. 1H-NMR (500 MHz, d6-DMSO) δ12.38 (s br, 1H), 8.38 (s, 1H), 7.95 (d, 3.5 Hz, 1H), 6.61 (d, 3.5 Hz, 1H). MS: m/z 197.9/199.9 [MH+].

後処理

  1. temperatureat reflux for 15 hours
  2. concentrationthe reaction mixture was concentrated in vacuum and water
  3. additionadded
  4. extractionThe aqueous layer was extracted three times with dichloromethane
  5. customPurification by silica gel chromatography with a gradient of ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-b64e62c9d157427991f421ad0397a96f
出典データセット
uspto-grants-2008_11
特許番号
US07452993B2

反応ノート

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