Water → HCID 70839153, compound

HRID 1952369Notes

Reaction equation

HRID 1952369 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[C:18](Br)[CH:19]=1)[O:5][C:6]1[C:7](=[O:16])[NH:8][CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].[Cu][C:22]#[N:23].[CH3:24][N:25]1CCCC1=O.O>C(OCC)(=O)C>[O:16]=[C:7]1[C:6]([O:5][C:4]2[CH:3]=[C:2]([C:22]#[N:23])[CH:19]=[C:18]([CH:17]=2)[C:24]#[N:25])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:9][NH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 59529753HCID 59529753, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 70839153HCID 70839153, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

To a high pressure vessel charged with 3-(3,5-dibromophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one (0.200 g, 0.484 mmol) and copper(I) cyanide (0.434 g, 4.84 mmol) was added N-methylpyrrolidinone (2 mL). The vessel was sealed and placed in an oil bath heated to 175° C. After 90 minutes, the reaction mixture was allowed to cool to room temperature. Water (25 mL) and ethyl acetate (50 mL) were added to the reaction mixture. This mixture was filtered through diatomaceous earth and the filtrate layers were separated. The aqueous layer was extracted with ethyl acetate (50 mL). The combined organic extracts were washed with brine (2×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was adsorbed onto silica gel and purified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column, eluting with 0-5% methanol in CH2Cl2 to afford the title compound. 1H NMR (DMSO-d6) δ 12.72 (s, 1H), 8.16-8.14 (m, 1H), 8.02-7.98 (m, 2H), 7.61 (d, J=7.0 Hz, 1H), 6.50 (d, J=6.9 Hz, 1H). LRMS (M+1)=305.9.

Workup

  1. customThe vessel was sealed
  2. customplaced in an oil bath
  3. temperatureto cool to room temperature
  4. filtrationThis mixture was filtered through diatomaceous earth
  5. customthe filtrate layers were separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
  7. washThe combined organic extracts were washed with brine (2×50 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. custompurified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column
  12. washeluting with 0-5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-23b651135023458d839fd052067d1e5b
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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