Dimethylformamide → HCID 57636776, compound

HRID 2110986Notes

Reaction equation

[H-].[Na+].CN(C)C=O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].Br[C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[N:21][CH:22]=1>O>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[N:21][CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.7 mmol) was mixed with 3-5 ml of dry dimethylformamide and 2-fluorophenol (0.24 ml, 2.7 mmol) was added to the stirred suspension. When the gas evolution was ceased the reaction mixture was heated at stirring at 60° C. and 5-bromo-2-nitropyridine (0.5 g, 2.5 mmol) was added to the reaction mixture in one portion. The reaction mixture was stirred at 60° C. for about 12 hours. The reaction mixture was then mixed with 50 ml of water and extracted into methylene chloride (3×20 ml). Organic extract was washed with water and brine, dried over magnesium sulfate and concentrated by rotary evaporation. The resulting mixture was purified by column chromatography on silica (30 g, EtOAc/hexane 1:3) to give 326 mg (57% yield) of desired product.

Workup

additionwas added to the stirred suspension
temperaturewas heated
stirringThe reaction mixture was stirred at 60° C. for about 12 hours
extractionextracted into methylene chloride (3×20 ml)
extractionOrganic extract
washwas washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated by rotary evaporation
customThe resulting mixture was purified by column chromatography on silica (30 g, EtOAc/hexane 1:3)

Sources & evidence

ORD record: ord-12bd470f71ed4f229399b0b242bf480b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517992B2

Reaction notes

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