Cesium carbonate → HCID 78321547, compound

HRID 1752975Notes

Reaction equation

HRID 1752975 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].F[C:8]1[CH:23]=[C:22]([C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[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:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([O:39][CH3:40])[CH:33]=1.O.C(OCC)(=O)C>CN1C(=O)CCC1>[F:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:8]2[CH:23]=[C:22]([C:24]([F:30])([F:29])[C:25]([F:26])([F:27])[F:28])[CH:21]=[CH:20][C:9]=2[C:10]([NH:12][C:13]2[CH:18]=[CH:17][NH:16][C:15](=[O:19])[CH:14]=2)=[O:11])=[C:34]([O:39][CH3:40])[CH:33]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 27373684-Fluoro-2-methoxyphenolHCID 22728543Water ethylacetateHCID 86728476HCID 86728476, compound

Product 1

HCID 78321547HCID 78321547, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Cs2CO3 (69.8 mg, 0.21 mmol) was added to a solution of 2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)-4-(perfluoroethyl)benzamide (25 mg, 0.07 mmol) and 4-fluoro-2-methoxyphenol (24.4 μL, 0.2 mmol) in NMP (0.3 mL) and the reaction was stirred at 100° C. for 45 minutes. The reaction mixture was poured into water:ethyl acetate (9:1). The mixture was shaken, and the solid was filtered off, washed with ether, then triturated with ethyl acetate and dried to give the desired product. The mother liquors were filtered and washed with ethyl acetate to give a second crop of material. Both solids were combined and dried under vacuum to give 2-(4-fluoro-2-methoxy-phenoxy)-N-(2-oxo-1H-pyridin-4-yl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide (2a) (15.4 mg, 45%) as a white solid. ESI-MS m/z calc. 472.08, found 473.3 (M+1)+; Retention time: 1.62 minutes. 1H NMR (400 MHz, DMSO-d6) δ 11.32 (s, 1H), 10.62 (s, 1H), 7.83 (d, J=7.9 Hz, 1H), 7.51 (d, J=7.9 Hz, 1H), 7.39-7.27 (m, 2H), 7.17 (dd, J=10.7, 2.8 Hz, 1H), 6.88 (dd, J=11.3, 5.7 Hz, 1H), 6.81 (s, 1H), 6.75 (s, 1H), 6.43 (d, J=7.1 Hz, 1H), 3.73 (s, 3H) ppm.

Workup

  1. stirringThe mixture was shaken
  2. filtrationthe solid was filtered off
  3. washwashed with ether
  4. customtriturated with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-cda105b3e88e44849abf73f266dbf91c
Source dataset
uspto-grants-2015_10
Patent number
US09163042B2

Reaction notes

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