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

HRID 272046노트

반응식

HRID 272046 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-b64e62c9d157427991f421ad0397a96f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452993B2

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