N-bromobutanimide → tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

HRID 595901노트

반응식

HRID 595901 반응식
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 22046506tert-Butyl (5-methylpyrazin-2-yl)carbamate

생성물 1

HCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
85 °C

실험 절차

A solution of tert-butyl 5-methylpyrazin-2-ylcarbamate (2.79 g, 13.33 mmol), NBS (2.61 g, 14.67 mmol) and AlBN (0.219 g, 1.33 mmol) in CCl4 (45 mL) was purged with Argon, then the solution was heated with 85° C. oil bath for 4 h. The reaction mixture was cooled to room temperature, concentrated and the residue was redissolved in EtOAc (˜50 mL), washed with dilute aqueous NaOH twice (10 mL 1 N NaOH diluted in 20 mL H2O), brine (30 mL), dried (Na2SO4) and concentrated. The residue was further purified by flash chromatography on silica gel eluted with gradient EtOAc/CH2Cl2 (0-30%) and tert-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate was obtained in off-white solid. LCMS (m/z): 288.1/290.1 (MH+), 0.82 min; 1H NMR (400 MHz, CDCl3) δ ppm 9.26 (s, 1H), 8.32 (d, J=1.2 Hz, 1H), 7.62 (br. s., 1H), 4.56 (s, 2H), 1.56 (s, 9H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionthe residue was redissolved in EtOAc (˜50 mL)
  4. washwashed with dilute aqueous NaOH twice (10 mL 1 N NaOH diluted in 20 mL H2O), brine (30 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was further purified by flash chromatography on silica gel
  8. washeluted with gradient EtOAc/CH2Cl2 (0-30%)

출처 및 근거

ORD 기록
ord-4443b3e244824b1f9506d440f4c513ac
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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