Sodium Azide → Methyl 2-(4-azido-3-cyanophenyl)isonicotinate

HRID 562902Notes

Reaction equation

HRID 562902 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1F)#[N:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[N:20]([C:8]1[CH:7]=[CH:6][C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[C:1]#[N:2])=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 66995083Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate

Product 1

HCID 86626138Methyl 2-(4-azido-3-cyanophenyl)isonicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate and sodium azide were dissolved in a DMF solution, followed by stirring at 50° C. for 4 hours to obtain methyl 2-(4-azido-3-cyanophenyl)isonicotinate. NMRC: 7.38 (1H, d), 7.84 (1H, dd), 8.46 (1H, d)

Sources & evidence

ORD record
ord-2b602ad16214468eb29c347fe90aa8f1
Source dataset
uspto-grants-2011_11
Patent number
US08067446B2

Reaction notes

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