HCID 90438198, compound → HCID 90413080, compound

HRID 573832Notes

Reaction equation

HRID 573832 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[N:9]=2)[CH:5]=[CH:4][C:3]=1/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27]>[OH-].[OH-].[Pd+2].C(O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:17][CH:18]=3)[N:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 1

HCID 90438198HCID 90438198, compound

Product 1

HCID 90413080HCID 90413080, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 9942167Palladium hydroxideSolvent

Procedure

The title compound was prepared from (E)-ethyl 3-(2-fluoro-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acrylate (CB13) using palladium hydroxide on carbon and ethanol as solvent; isolated as a tan solid (0.871 g, 67%, 85% pure): 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 7.92-7.82 (m, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.43-7.36 (m, 2H), 7.32 (t, J=7.8 Hz, 1H), 4.14 (q, J=7.1 Hz, 2H), 3.03 (t, J=7.7 Hz, 2H), 2.67 (dd, J=8.2, 7.2 Hz, 2H), 1.24 (t, J=7.1 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ (376 MHz, CDCl3) δ −58.03, −117.98; ESIMS m/z 423 ([M]+).

Workup

  1. customisolated as a tan solid (0.871 g, 67%, 85% pure)

Sources & evidence

ORD record
ord-a96a8228d2f44158a72166a68eb63f8d
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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