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

HRID 875162Notes

Reaction equation

HRID 875162 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-b2a308ed7e4b45f7860d6821fdb0ca9a
Source dataset
uspto-grants-2015_03
Patent number
US08981106B2

Reaction notes

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