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

HRID 333151ノート

反応式

HRID 333151 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 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide [Intermediate AR] (2.6 g, 8.4 mmol) and tetrabutylammonium fluoride [1 M in THF] (18 mL, 18 mmol) in anhydrous THF (26 mL) was heated at 75° C. for 20 h, after which it was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo to yield a residue that was purified via silica gel chromatography eluting with 30% EtOAc in hexanes to give the title compound as a tan solid (0.69 g, 42%). 1H NMR (CDCl3, 300 MHz): δ 8.88 (bs, 1H), 8.34 (s, 1H), 7.62 (t, J=3.3 Hz, 1H), 6.71 (dd, J=3.6 Hz, 3.9 Hz, 1H). HPLC retention time: 1.73 minutes. MS ESI (m/z): 198.2, 200.2 (M+H)+, calc. 197.

後処理

  1. customafter which it was partitioned between EtOAc and H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customto yield a residue that
  6. customwas purified via silica gel chromatography
  7. washeluting with 30% EtOAc in hexanes

出典と根拠

ORDレコード
ord-3db43d6315094affac5922c2564f752d
出典データセット
uspto-grants-2014_11
特許番号
US08877772B2

反応ノート

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