Cesium carbonate → HCID 78320905, compound

HRID 2170441Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].F[C:8]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][NH:16][C:15](=[O:19])[CH:14]=1)=[O:11].[F:25][C:26]([F:36])([F:35])[O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>CN(C=O)C>[F:24][C:21]1[CH:22]=[CH:23][C:8]([O:34][C:31]2[CH:32]=[CH:33][C:28]([O:27][C:26]([F:25])([F:35])[F:36])=[CH:29][CH:30]=2)=[C:9]([CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][NH:16][C:15](=[O:19])[CH:14]=1)=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

Cs2CO3 (146.6 mg, 0.45 mmol) was added to a solution of 2,5-difluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (37.5 mg, 0.15 mmol) and 4-trifluoro methoxyphenol (80.1 mg, 0.45 mmol) in DMF (0.9 mL) and the reaction was stirred at 100° C. for 8 hours. The reaction was filtered and purified by reverse phase HPLC using a gradient of acetonitrile in water (10-99%) and HCl as a modifier to yield 5-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)-2-(4-(trifluoromethoxy)phenoxy)benzamide (101) (1.9 mg, 3%). ESI-MS m/z calc. 408.07. found 409.3 (M+1)+; Retention time: 1.68 minutes (3 minutes run).

Workup

filtrationThe reaction was filtered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-f99c8f2d03a74f29a22c6b2536c15e08
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051270B2

Reaction notes

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