Chloroform → 4-Bromo-1-methoxyisoquinoline

HRID 1921328노트

반응식

HRID 1921328 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1C.[CH:14](Cl)(Cl)Cl.IC>C(=O)([O-])[O-].[Ag+2].C(N(CC)CC)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:14])=[N:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6212ChloroformHCID 6328Methyl iodideHCID 67492305HCID 67492305, 화합물

생성물 1

HCID 247666564-Bromo-1-methoxyisoquinoline수율 60%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 8471Triethylamine용매

실험 절차

To a stirred suspension of 4-bromo-3-methyl-2H-isoquinolin-1-one (1.86 g, 7.81 mmol), silver carbonate (2.92 g, 10.6 mmol) and chloroform (150 mL) is added dropwise over 10 min iodomethane (7.3 mL, 117 mmol) and the mixture is stirred in the dark for 3 d. Triethylamine is added and the solids are removed by filtration through a pad of Celite. The filtrate is concentrated and the residue is purified by chromatography eluting with dichloromethane. Product containing fractions are combined and concentrated to afford 4-bromo-1-methoxyisoquinoline (1.19 g, 60% yield) as an oil that solidified on standing. LC/MS: MS m/e=252/254 (M+H); RT 4.68; 1H NMR (CDCl3, δ ppm) 8.19 (1H, d), 8.09 (1H, d), 7.71 (1H, t), 7.50 (1H, t), 4.10 (3H, s); 2.71 (3H, s).

후처리

  1. customthe solids are removed by filtration through a pad of Celite
  2. concentrationThe filtrate is concentrated
  3. customthe residue is purified by chromatography
  4. washeluting with dichloromethane
  5. additionProduct containing fractions
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-86b3369fd6614ea9a04def80da64e725
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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