4-Fluoro-N-methylaniline → HCID 61062518, compound

HRID 404763Notes

Reaction equation

HRID 404763 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([NH:16][CH3:17])=[CH:14][CH:13]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:16]([C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[CH3:17])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 680244-Fluoro-N-methylanilineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 61062518HCID 61062518, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-Chloronicotinoyl chloride (353 mg, 2.0 mmol) was dissolved in anhydrous DMF (2 mL) and slowly added to a stirring solution of 4-fluoro-N-methylaniline (242 μL, 2.0 mmol) and DBU (300 μL, 2.0 mmol) in anhydrous DMF (2 mL). After 90 minutes, the DMF was removed in vacu and the reaction was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried over sodium sulfate, filtered, and dried in vacu. The crude solid was purified by silica plug (1:1 ethyl acetate/hexanes) to yield 6-Chloro-N-(4-fluoro-phenyl)-N-methyl-nicotinamide as an off-white, glassy solid (411 mg, 77%).

Workup

  1. customthe DMF was removed in vacu
  2. customthe reaction was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customdried in vacu
  7. customThe crude solid was purified by silica plug (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a522573913e24fc2ac9a1b6c0e892f3b
Source dataset
uspto-grants-2014_06
Patent number
US08748623B2

Reaction notes

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