1,10-Phenanthroline → 5-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrile

HRID 2093570Notes

Reaction equation

HRID 2093570 reaction equation
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1.[N:15]1C2C(=CC=C3C=2N=CC=C3)C=C[CH:16]=1.C([Cu])#N>CC(N(C)C)=O>[N+:12]([C:5]1[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]([C:16]#[N:15])=[N:3][CH:4]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 13181,10-PhenanthrolineHCID 534863502-Bromo-5-nitro-3-(trifluoromethyl)pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 218748935-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

The crude 2-bromo-5-nitro-3-(trifluoromethyl)pyridine 21 is dissolved in dimethylacetamide (DMA) and phenanthroline (0.2 equivalents) is added. The mixture is heated to 160° C. and CuCN (2 equivalents) is added. The mixture is stirred for 40 minutes. Chromatography is performed to produce the 5-nitro-3-(trifluoromethyl)pyridine-2-carbonitrile 22 in a yield of 67%.

Sources & evidence

ORD record
ord-da65ae6c13e64b979468e592764c11b2
Source dataset
uspto-grants-2013_05
Patent number
US08445507B2

Reaction notes

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