Sodium Carbonate → 5-(4-(Methylsulfonyl)phenyl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amine

HRID 78571Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:3]=[C:4]([C:9]3[N:13]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[O:11][N:10]=3)[C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:26][CH:25]=1)(=[O:23])=[O:22]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amine (100 mg, 0.3143 mmol), (4-methylsulfonylphenyl)boronic acid (94.29 mg, 0.4714 mmol) and PdCl2(PPh3)2 (11.03 mg, 0.01572 mmol) in DMF (2 mL) was treated with Na2CO3 (471.4 μL of 2 M, 0.9429 mmol) and the reaction placed under an atmosphere of nitrogen and heated at 110° C. in a sealed tube for 16 hours. The resultant precipitate was filtered, washed with water and dried under vacuum (83 mg, 67% Yield).

Workup

filtrationThe resultant precipitate was filtered
washwashed with water
customdried under vacuum (83 mg, 67% Yield)

Sources & evidence

ORD record: ord-6eb2f27cfd7a4843aa921662fb933b66
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841308B2

Reaction notes

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