Sodium Carbonate → 3-(Pyridin-2-yl)-5-[5-(5-pyrimidyl)-pyrid-3-yl]-1,2,4-oxadiazole

HRID 431939Notes

Reaction equation

HRID 431939 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[C:16](Br)[CH:17]=2)[O:9][N:8]=1.[N:19]1[CH:24]=[C:23](B(O)O)[CH:22]=[N:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:23]3[CH:24]=[N:19][CH:20]=[N:21][CH:22]=3)[CH:17]=2)[O:9][N:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 114266383-(Pyridin-2-yl)-5-(5-bromopyrid-3-yl)-1,2,4-oxadiazole

Product 1

HCID 99661533-(Pyridin-2-yl)-5-[5-(5-pyrimidyl)-pyrid-3-yl]-1,2,4-oxadiazoleYield 7.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a similar fashion, 3-(2-pyridyl)-5-(5-bromo-pyrid-3-yl)-1,2,4-oxadiazole (42 mg, 0.1385 mmole), 5-pyrimidylboronic acid (26.6 mg,0.208 mmole) and Pd(PPh3)4 (23.99 mg, 0.021 mmole) in a solution of 2M sodium carbonate (1.5 mL) and ethylene glycol dimethyl ether (1.5 mL) was heated overnight at 105° C. Standard workup afforded 3.2 mg (8%) of 3-(2-pyridyl)-5-[5-(5-pyrimidyl)-pyrid-3-yl ]-1,2,4-oxadiazole (3.2 mg, 7.6%).

Sources & evidence

ORD record
ord-0c28e47234a84fc4bf2a482aeed2dc88
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

Loading…