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

HRID 2170436Notes

Reaction equation

[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].F[C:8]1[CH:23]=[C:22]([Cl:24])[CH:21]=[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]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=1OC>CN(C=O)C>[Cl:24][C:22]1[CH:21]=[CH:20][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][NH:16][C:15](=[O:19])[CH:14]=2)=[O:11])=[C:8]([O:32][C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][C:28]=2[O:4][CH3:1])[CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Cs2CO3 (651.6 mg, 2.0 mmol) was added to a solution of 2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)-4-chlorobenzamide (53.3 mg, 0.20 mmol) and 4-fluoro-3-methoxyphenol (284.3 mg, 2.0 mmol) in DMF (1 mL) and the reaction was stirred at 100° C. for 1 hour. 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-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (16) (22.1 mg, 28%). ESI-MS m/z calc. 388.06. found 389.15 (M+1)+; Retention time: 1.53 minutes (3 minutes run).

Workup

filtrationThe reaction was filtered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-9682f34850894ca197ff61c2318e88c8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051270B2

Reaction notes

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