N-bromobutanimide → Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409424노트

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HRID 1409424 반응식
[CH3:1][Si:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]=[CH:8]1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:25][C:8]1[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:16])([CH3:17])[CH3:1])[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 22954042Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

생성물 1

HCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6547Azobisisobutyronitrile용매

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온도
65 °C

실험 절차

Into a flask containing methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (4.0 g; 15.6 mmol) in CCl4 (100 ml), catalytic AIBN, NBS (3.1 g, 17.1 mmol) were added and stirred at 65° C. for 3 h. The reaction mixture was quenched with aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was concentrated and purified by column chromatography. Yield 3.5 g. 1H-NMR (400 MHz; DMSO-d6): δ 0.04 (s, 9H), 0.84 (t, 2H), 3.53 (t, 2H), 3.75 (s, 3H), 5.30 (s, 2H), 8.25 (s, 1H). LC-MS: [M+1]=335.01.

후처리

  1. additionwere added
  2. customThe reaction mixture was quenched with aqueous solution of NaHCO3
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-f082c59adbd7488aa1ed071cea174464
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921378B2

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