Pyridine → HCID 58958118, compound

HRID 914968Notes

Reaction equation

HRID 914968 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[Cl:14].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][CH2:26][CH:27]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[CH2:30][CH2:29][NH:28]2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].N1C=CC=CC=1>C1COCC1>[Cl:14][C:6]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:28]1[CH2:29][CH2:30][C:31]2[C:36](=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[CH:27]1[CH2:26][CH2:25][C:19]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([O:16][CH3:15])[CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3097182-(2-Bromo-ethoxy)-1-chloro-4-nitrobenzeneHCID 12934313HCID 12934313, compound

Product 1

HCID 58958118HCID 58958118, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15 (315 mg, 1.13 mmol) in anhydrous THF (3 mL) were sequentially added 1-(2-(3,4-dimethoxy-phenyl)-ethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline (16, Morimoto et al, Heterocycles 1996 43:2557; Brossi et al, Helv Chim Acta 1960 43:1459; Meyers et al, Tetrahedron Lett 1981 22:5115; Meyers et al, J Am Chem Soc 1983 105:117) (404 mg, 1.13 mmol) and pyridine (0.3 mL). The reaction mixture was heated under reflux for 2 days before it was partitioned between EtOAc and water (20 mL each). The organic layer was separated, washed with water (15 mL), brine (15 mL), and dried over Na2SO4. The solids were filtered and the filtrate was purified by chromatography (silica gel) eluting with hexanes:EtOAc (1:1) to give 17 (205 mg)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 days before it
  3. customwas partitioned between EtOAc and water (20 mL each)
  4. customThe organic layer was separated
  5. washwashed with water (15 mL), brine (15 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationThe solids were filtered
  8. customthe filtrate was purified by chromatography (silica gel)
  9. washeluting with hexanes:EtOAc (1:1)

Sources & evidence

ORD record
ord-7cee0ed689584f1e84d127e7b87e5a99
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

Loading…