Water → 3-bromo-5-(3-methyl-1,2,4-oxadiazol-5-yl)Pyridine

HRID 1455641Notes

Reaction equation

HRID 1455641 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.O[N:24]=[C:25]([NH2:27])[CH3:26].O>CN(C=O)C.N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:7]2[O:9][N:27]=[C:25]([CH3:26])[N:24]=2)[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 30926N-HydroxyacetamidineHCID 682631,1'-CarbonyldiimidazoleHCID 887075-Bromonicotinic acid

Product 1

HCID 529037353-bromo-5-(3-methyl-1,2,4-oxadiazol-5-yl)Pyridine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5-bromo nicotinic acid(1.0 eq.) and CDI (1.1 eq) in DMF (0.25M) was stirred at 20° C. for 5 min and then N′-hydroxy ethanimidamide (1.1 eq) in pyridine (0.6 M) was added. The reaction mixture was stirred at 110° C. for 15 h, cooled to rt and poured into water. The title compound was isolated by filtration as a solid.

Workup

  1. stirringThe reaction mixture was stirred at 110° C. for 15 h
  2. temperaturecooled to rt

Sources & evidence

ORD record
ord-8981e2f61e7b470ea2142b78ed53d923
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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