2-Mercaptoethanol → 3-{[(2-Hydroxyethyl)thio]methyl}-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

HRID 2233053노트

반응식

HRID 2233053 반응식
Br[CH2:2][C:3]1[N:4]([CH3:22])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2.[OH:23][CH2:24][CH2:25][SH:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:23][CH2:24][CH2:25][S:26][CH2:2][C:3]1[N:4]([CH3:22])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2

참가 물질

5

반응물 3

HCID 15672-MercaptoethanolHCID 10796Cesium carbonateHCID 225559473-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

생성물 1

HCID 113826983-{[(2-Hydroxyethyl)thio]methyl}-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (125 mg, 0.349 mmol) in 5 mL of dimethylformamide was added 2-hydroxyethanethiol (0.027 mL, 0.38 mmol) and cesium carbonate (227 mg, 0.698 mmol). After one hour, the reaction mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by recrystallization from EtOAc/hexane to provide the titled product. 1H-NMR (500 MHz, CDCl3) δ 8.41 (d, J=9.0 Hz, 1H), 7.45-7.54 (m, 3H), 7.34-7.36 (m, 2H), 7.04 (dd, J=9.0, 2.5 Hz, 1H), 6.35 (d, J=2.5 Hz, 1H), 3.83, (s, 3H), 3.68 (s, 3H), 3.63 (s, 2H), 3.41 (m, 2H), 2.58 (t, J=5.6 Hz, 2H) ppm. ESI+ MS: 356.14 [M+H]+.

후처리

  1. customthe reaction mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by recrystallization from EtOAc/hexane

출처 및 근거

ORD 기록
ord-06a6014d45a14898b4a339fe21433c65
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709476B2

반응 노트

불러오는 중…