Sodium hydride → HCID 86678203, compound

HRID 1747552Notes

Reaction equation

Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:3]=1.[F:16][C:17]([F:27])([F:26])[CH:18]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[OH:19].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[Cl:12][C:11]1[C:2]([O:19][CH:18]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:17]([F:16])([F:26])[F:27])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: -78 °C

Procedure

In THF (200 mL) was dissolved 2,3-dichloro-6-nitroquinoxaline (4.00 g, 16.4 mmol) and the mixture was cooled to −78° C. To the solution were added 2,2,2-trifluoro-1-(pyridin-3-yl)ethanol (3.05 g, 17.2 mmol) obtained in Step 1 and sodium hydride (1.31 g, 32.8 mmol) and the mixture was stirred at −78° C. allowing the temperature to rise slowly to −30° C. over 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2) to give 3-chloro-6-nitro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy) quinoxaline (3.98 g, 63% yield).

Workup

extractionExtraction with ethyl acetate
washwashing with saturated brine
dry with materialdrying over anhydrous magnesium sulfate
filtrationAfter filtration
customthe solvent in the filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2)

Sources & evidence

ORD record: ord-c60c47612e3343c6aa9a0d3d5a4fbb1a
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150569B2

Reaction notes

Loading…