Sodium Bicarbonate → HCID 86715658, compound

HRID 1507302Notes

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:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1)=[C:5]2[Cl:24].C[O-].[Na+].[C:28](=O)(O)[O-:29].[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:29][CH3:28])[C:6]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1)=[C:5]2[Cl:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-bromo-2,4-dichloro-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinoline (1.0 g, 2.3 mmol, Intermediate 9: step b) and sodium methoxide (1.2 g, 22 mmol) in dry toluene (12 mL) was heated to 80° C. under a positive pressure of nitrogen overnight. The mixture was allowed to cool to ambient temperature. Aqueous saturated sodium bicarbonate solution was added to the mixture and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to dryness. The crude material was purified by flash column chromatography (silica gel, 0-20% EtOAc-hexane) to provide the title compound as a white solid.

Workup

temperatureto cool to ambient temperature
customthe layers were separated
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated to dryness
customThe crude material was purified by flash column chromatography (silica gel, 0-20% EtOAc-hexane)

Sources & evidence

ORD record: ord-830ed15c5bde408d94fe653d0b052669
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221804B2

Reaction notes

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