Dimethylformamide → 3-(2-Pyridyl)-5-(5-methylpyrid-3-yl)-1,2,4-oxadiazole

HRID 2216806Notes

Reaction equation

HRID 2216806 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].C[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:20]=1)C(O)=O.C([N:23]([CH2:26]C)CC)C.C[N:29](C)C=O>ClCCl>[N:14]1[CH:13]=[CH:12][CH:20]=[CH:16][C:15]=1[C:26]1[N:23]=[C:7]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)[O:8][N:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2562085-Methylnicotinic acidHCID 145380555-Methylnicotinoyl chloride

Product 1

HCID 99647333-(2-Pyridyl)-5-(5-methylpyrid-3-yl)-1,2,4-oxadiazoleYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion, 5-methylnicotinoyl chloride was prepared from 5-methylnicotinic acid (548 mg, 4 mmoles). Treatment of the acid chloride with pyrid-2-ylamidoxime (822 mg, 6 mmol) and triethylamine (1.2 g, 12 mmol) in dichloromethane (6 mL), followed by heating in dimethylformamide (6 mL) at 120° C. for 2.5 hours, afforded 448 mg (47%) of 3-(2-pyridyl)-5-(5-methyl-pyrid-3-yl)-1,2,4-oxadiazole.

Sources & evidence

ORD record
ord-ae03c8a4217944e582e2abecaf8d1f5a
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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