Methanol → 6-Methoxy-3-(methoxymethyl)-2-methyl-4-phenylisoquinolin-1(2H)-one

HRID 2233052ノート

反応式

HRID 2233052 の反応式
[CH3:1][OH:2].[H-].[Na+].Br[CH2:6][C:7]1[N:8]([CH3:26])[C:9](=[O:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][C:13]([O:23][CH3:24])=[CH:12][CH:11]=2>CN(C)C=O>[CH3:24][O:23][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:25])[N:8]([CH3:26])[C:7]([CH2:6][O:2][CH3:1])=[C:16]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 225559473-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

生成物 1

HCID 112782896-Methoxy-3-(methoxymethyl)-2-methyl-4-phenylisoquinolin-1(2H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of methanol (0.057 mL, 1.40 mmol) in 2 mL of dimethylformamide was added sodium hydride (45 mg, 60% dispersion in mineral oil, 1.11 mmol). After 10 minutes, 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one was added (100 mg, 0.279 mmol). After 30 minutes, the reaction mixture was cooled to 0° C., and quenched with 1 mL of saturated NaHCO3 solution. The mixture was partitioned between EtOAc and saturated NaHCO3 solution, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography through SiO2 (50% EtOAc/hexane) to provide the titled product as a white solid. 1H-NMR (500 MHz, CDCl3) δ 8.43 (d, J=9.0 Hz, 1H), 7.44-7.50 (m, 3H), 7.29-7.31 (m, 2H), 6.91 (dd, J=9.0, 2.5 Hz, 1H), 6.42 (d, J=2.5 Hz, 1H), 4.18 (s, 2H), 3.75, (s, 3H), 3.69 (s, 3H), 3.24 (s, 3H) ppm. ESI+ MS: 310.23 [M+H]+.

後処理

  1. waitAfter 30 minutes
  2. customquenched with 1 mL of saturated NaHCO3 solution
  3. customThe mixture was partitioned between EtOAc and saturated NaHCO3 solution
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography through SiO2 (50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-71714bbd1b994b68a931cc69b02d834a
出典データセット
uspto-grants-2010_05
特許番号
US07709476B2

反応ノート

読み込み中…