Dimethylformamide → 2-fluoro-4-methoxy-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339575Notes

Reaction equation

HRID 339575 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C=O)C.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([CH:25]=[C:26]([C:28]3[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=3)[N:27]=2)[CH:24]=1.CCOC(C)=O>S(Cl)(Cl)=O.N1C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:32][C:31]1[CH:30]=[CH:29][C:28]([C:26]2[N:27]=[C:22]3[CH:21]=[CH:20][C:19]([CH3:18])=[CH:24][N:23]3[CH:25]=2)=[CH:34][CH:33]=1)=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)anilineHCID 27745422-Fluoro-4-methoxybenzoic acid

Product 1

HCID 583419772-fluoro-4-methoxy-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamideYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A stirred solution of 2-fluoro-4-methoxybenzoic acid (0.23 g, 1.34 mmol) in thionyl chloride (7 ml) containing a drop of DMF was heated under reflux for 4 h. The excess reagent was then removed under reduced pressure to give a crude solid. The amide was prepared as described in the Amide Coupling section using the crude solid and 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.30 g, 1.34 mmol) in dry pyridine (15 ml) to give the title compound (0.323 g, 80%) as a colourless solid after work-up and flash chromatography (EtOAc).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customThe excess reagent was then removed under reduced pressure
  4. customto give a crude solid
  5. customThe amide was prepared

Sources & evidence

ORD record
ord-3fd8ef6692d0443481f0906cd83965d0
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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