Water → HCID 86655254, compound

HRID 1890293Notes

Reaction equation

HRID 1890293 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([Cl:25])[N:17]=1.O>C1COCC1>[Cl:25][C:18]1[N:17]=[C:16]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([F:3])=[CH:5][C:6]=2[C:11]([F:12])([F:13])[F:14])[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 678534-Fluoro-2-(trifluoromethyl)anilineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 86655254HCID 86655254, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.124 g, 5.18 mmol) was added to a chilled (0° C.) solution of 4-fluoro-2-(trifluoromethyl)aniline (0.464 g, 2.59 mmol) in THF (1 mL) and stirred for 30 min. 2,6-Dichloro-3-nitropyridine (0.500 g, 2.59 mmol) was then added and the reaction mixture stirred at 80° C. for 18 h. Water was added to quench excess sodium hydride and volatile solvents were removed under reduced pressure. The product was then extracted into DCM, solvent removed under reduced pressure, and the residue purified by preparative HPLC to give the title compound (0.624 g). LCMS m/z=336.0 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 6.87 (d, J=8.6 Hz, 1H), 7.34 (td, J1=8.4 Hz, J2=3.0 Hz, 1H), 7.43 (dd, J1=8.4 Hz, J2=3.0 Hz, 1H), 7.94 (dd, J1=9.0 Hz, J2=5.0 Hz, 1H), 8.49 (d, J=8.6 Hz, 1H), 10.26 (br s, 1H).

Workup

  1. stirringthe reaction mixture stirred at 80° C. for 18 h
  2. customto quench excess sodium hydride and volatile solvents
  3. customwere removed under reduced pressure
  4. extractionThe product was then extracted into DCM, solvent
  5. customremoved under reduced pressure
  6. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-b8a824355ee440f888f527b40287cc22
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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