2-Mercaptoethanol → HCID 11382698, compound

HRID 2233053Notes

Reaction equation

HRID 2233053 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 11382698HCID 11382698, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-06a6014d45a14898b4a339fe21433c65
Source dataset
uspto-grants-2010_05
Patent number
US07709476B2

Reaction notes

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