N-bromobutanimide → ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1508497노트

반응식

HRID 1508497 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:13][C:6]1[N:2]([CH3:1])[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:5]=1[CH3:7]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 14296950ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

생성물 1

HCID 67516409ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

To a solution of ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate (63 mg, 0.377 mmol) in CHCl3 (3.5 mL) at 0° C. was added N-bromosuccinimide (67.1 mg, 0.377 mmol). The reaction was stirred at 0° C. for 15 min. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate. LCMS calc.=245.0. found=245.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.83 (s, 1H); 4.27 (q, J=7.1 Hz, 2H); 3.91 (s, 3H); 2.05-2.02 (m, 3H); 1.34 (t, J=7.1 Hz, 3H).

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))

출처 및 근거

ORD 기록
ord-7fb169b1beb84f2d9e71975dec1c2979
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221834B2

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