Water → 5-Bromo-1,3-dimethoxyisoquinoline

HRID 2090059ノート

反応式

HRID 2090059 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5](Cl)[N:6]=[C:7]2[O:12][CH3:13].[CH3:15][O-:16].[Na+].O>CS(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([O:16][CH3:15])[N:6]=[C:7]2[O:12][CH3:13]

参加物

5

反応物 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 583494645-Bromo-3-chloro-1-methoxyisoquinoline

生成物 1

HCID 673101605-Bromo-1,3-dimethoxyisoquinoline

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 5-bromo-3-chloro-1-methoxyisoquinoline (420 mg, 1.54 mmol) in DMSO (4.0 mL) was added NaOMe (0.5 M in MeOH, 4.0 mL, 2.0 mmol). The solution was heated at 90° C. for 1.5 hours in a microwave reactor. The mixture was poured into water then extracted with EtOAc. The organics were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 15% EtOAc/hexanes to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 8.15 (d, J=8.5 Hz, 1H), 7.87 (d, J=8.0 Hz, 1H); 7.18 (t, J=8.0 Hz, 1H), 6.85 (s, 11-1), 4.18 (s, 3H), 4.05 (s, 3H). LC6: 3.67 min, (M+H): 268.

後処理

  1. extractionthen extracted with EtOAc
  2. dry with materialThe organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 15% EtOAc/hexanes

出典と根拠

ORDレコード
ord-bc7939f2630c4804a079cb4ee3aa3582
出典データセット
uspto-grants-2013_05
特許番号
US08436015B2

反応ノート

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