Cesium carbonate → HCID 78321547, compound

HRID 2170439Notes

Reaction equation

HRID 2170439 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 (111) (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) 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-5fd7fac93126463cb28e2877114ed31f
Source dataset
uspto-grants-2015_06
Patent number
US09051270B2

Reaction notes

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