Cesium carbonate → 4-chloro-2-(2-chloro-4-fluorophenoxy)-5-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide

HRID 2170442Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[C:23]([F:24])=[CH:22][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][NH:18][C:17](=[O:21])[CH:16]=2)=[O:13])=[C:10](F)[CH:9]=1.[Cl:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[OH:34]>CN(C=O)C>[Cl:7][C:8]1[C:23]([F:24])=[CH:22][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][NH:18][C:17](=[O:21])[CH:16]=2)=[O:13])=[C:10]([O:34][C:28]2[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=2[Cl:26])[CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Cs2CO3 (244.4 mg, 0.75 mmol) was added to a solution of 4-chloro-2,5-difluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (71.2 mg, 0.25 mmol) and 2-chloro-4-fluorophenol (109.9 mg, 0.75 mmol) in DMF (2 mL) and the reaction was stirred at 100° C. for 1 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 4-chloro-2-(2-chloro-4-fluorophenoxy)-5-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (109) (22.8 mg, 27%). ESI-MS m/z calc. 410.00. found 411.2 (M+1)+; Retention time: 1.76 minutes (3 minutes run).

Workup

filtrationThe reaction was filtered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-6c7a41a71c9b4adebe409de2e6f3d467
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051270B2

Reaction notes

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