Dimethylformamide → 2-(5-Fluoro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 1445011Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O.[CH2:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][NH:24]1>O>[F:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([N:24]2[CH2:25][CH2:26][C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:23]2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-chloro-5-fluoro-3-nitropyridine (1.00 g, 5.66 mmol) prepared in Step 4 and sodium carbonate (1.25 g, 9.06 mmol) were added to anhydrous N,N-dimethylformamide (50 ml). 1,2,3,4-tetrahydroisoquinoline (712 μl, 5.66 mmol) was added to the reaction mixture. The reaction mixture was stirred for 1 hour at 100° C. and then cooled to room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer washed with a sodium chloride solution three times, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v) to give 1.34 g of the titled compound as yellow solid. (Yield: 86%).

Workup

temperaturecooled to room temperature
extractionwas then extracted with ethyl acetate
washThe organic layer washed with a sodium chloride solution three times
dry with materialdried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5

Sources & evidence

ORD record: ord-3c43657923864fffb53ff538da4017b8
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662832B2

Reaction notes

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