Sodium Methoxide → 4-((6-Bromo-4-chloro-2-methoxyquinolin-3-yl)methyl)benzonitrile

HRID 928789Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)=[C:5]2[Cl:22].[CH3:23][O-:24].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:24][CH3:23])[C:6]([CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)=[C:5]2[Cl:22]

Participants

Conditions

Temperature: 105 °C

Procedure

A heterogeneous mixture of 4-((6-bromo-2,4-dichloroquinolin-3-yl)methyl)benzonitrile (650 mg, 1.16 mmol, Intermediate 44: step c) and sodium methoxide (314 mg, 5.81 mmol) in dry toluene (2.2 mL) was heated at 105° C. After 9 hours, the mixture was cooled to ambient temperature and filtered through Celite®, rinsing with DCM. The filtrate was concentrated and the crude was purified by flash column chromatography (silica gel, 0-5% EtOAc-Hexanes) to provide the title compound as a white solid.

Workup

temperaturethe mixture was cooled to ambient temperature
filtrationfiltered through Celite®
washrinsing with DCM
concentrationThe filtrate was concentrated
customthe crude was purified by flash column chromatography (silica gel, 0-5% EtOAc-Hexanes)

Sources & evidence

ORD record: ord-520b9e0e8b364888a0d1fd7346df13a4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290476B2

Reaction notes

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