Potassium Carbonate → n-[4-Chloro-3-(trifluoromethyl)phenyl]-5-[4-(pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine trifluoroacetate salt

HRID 1994033Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:35]([O-:38])([O-])=[O:36].[K+].[K+].Br[C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1>CN(C=O)C.CO>[F:22][C:21]([F:24])([F:23])[C:35]([OH:38])=[O:36].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:42]4[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=4)=[CH:18][CH:19]=3)=[N:11][N:10]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 80 °C

Procedure

4-(5-{[4-chloro-3-(trifluoromethyl)-phenyl]amino}-1,3,4-oxadiazol-2-yl)phenol (100 mg, 0.281 mmol) was dissolved in ca. 2 mL of anhydrous DMF under argon. Solid potassium bis(trimethylsilyl)amide (140.2 mg, 0.702 mmol) was added and the resulting yellow solution was heated at 80° C. for 15 min. Then solid K2CO3 (19.4 mg, 0.140 mmol) was added, followed by 3-bromopyridine (89.0 mg, 0.562 mmol). The reaction mixture was microwaved at 250° C. for 10 min. Then it was diluted with 1 mL of MeOH, filtered and purified by preparative reverse-phase chromatography using acetonitrile/water with 0.1% TFA gradient. The major peak having the mass of the product was collected; solvent was removed in vacuo to give the title product as a brown oil (20.6 mg).

Workup

customThe reaction mixture was microwaved at 250° C. for 10 min
filtrationfiltered
custompurified by preparative reverse-phase chromatography
customwas collected
customsolvent was removed in vacuo

Sources & evidence

ORD record: ord-a406e69bd9684718a66b9e9ce3a8a8e6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652051B2

Reaction notes

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