Cesium carbonate → 4,5-Dichloro-N-(1,2-dihydro-2-oxo-4-pyridinyl)-2-(4-fluoro-2-methoxyphenoxy)benzamide

HRID 1053178Notes

Reaction equation

[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[C:23]([Cl: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.[F:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]=1OC>CN1C(=O)CCC1>[Cl:7][C:8]1[C:23]([Cl: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:33][C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][C:29]=2[O:4][CH3:1])[CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Cs2CO3 (97.7 mg, 0.3 mmol) was added to a solution of 4,5-dichloro-2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (30.1 mg, 0.1 mmol) and 4-fluoro-3-methoxyphenol (42.6 mg, 0.3 mmol) in NMP (0.5 mL) and the reaction was stirred at 90° C. for 2 hours. The reaction was filtered and purified by reverse phase HPLC using a gradient of acetonitrile in water (1-99%) and HCl as a modifier to yield 4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (114) (13.2 mg, 30%). ESI-MS m/z calc. 422.02. found 423.3 (M+1)+; Retention time: 1.57 minutes (3 minutes run).

Workup

filtrationThe reaction was filtered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-278c7a2428674c53a4b9e851b5a6017c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393235B2

Reaction notes

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