Toluene → 3-(Benzo[b]thiophen-2-ylmethyl)-6-bromo-4-chloro-2-methoxyquinoline

HRID 926525Notes

Reaction equation

HRID 926525 reaction equation
[S:1]1[C:5]([CH2:6][C:7]2[C:8](Cl)=[N:9][C:10]3[C:15]([C:16]=2[Cl:17])=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3)=[CH:4][C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]1=2.[CH3:24][O-:25].[Na+].C1(C)C=CC=CC=1>C(Cl)Cl>[S:1]1[C:5]([CH2:6][C:7]2[C:8]([O:25][CH3:24])=[N:9][C:10]3[C:15]([C:16]=2[Cl:17])=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3)=[CH:4][C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]1=2

Participants

5

Reactant 3

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 867155913-(Benzo[b]thiophen-2-ylmethyl)-6-bromo-2,4-dichloroquinoline

Product 1

HCID 867156033-(Benzo[b]thiophen-2-ylmethyl)-6-bromo-4-chloro-2-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A heterogeneous mixture of 3-(benzo[b]thiophen-2-ylmethyl)-6-bromo-2,4-dichloroquinoline (7.5 g, 17.73 mmol, Intermediate 51: step a), sodium methoxide (4.79 g, 88.62 mmol), and toluene (25 mL) was heated at 110° C. in a sealed tube for 6 hours. The resulting black tar was diluted with DCM, then filtered through Celite®, rinsing with dichloromethane. The filtrate was concentrated and the crude product purified by chromatography (heptanes/DCM, gradient) to provide the title compound as a tan solid.

Workup

  1. filtrationfiltered through Celite®
  2. washrinsing with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customthe crude product purified by chromatography (heptanes/DCM, gradient)

Sources & evidence

ORD record
ord-88bb014102b9464781b8661cf55c9a65
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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