Pyridine → 3-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic Acid Methyl Ester

HRID 335309Notes

Reaction equation

HRID 335309 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[F:29])[C:22]([O:24][CH3:25])=[O:23].N1C=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=3[F:29])[C:22]([O:24][CH3:25])=[O:23])=[O:13])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 12541234Methyl 3-amino-4-fluorobenzoateHCID 672614887-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 712828883-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (step 3) (1.8 g, approximately 7.47 mmol) and thionyl chloride (10 ml, 137 mmol) under N2 was heated at reflux for 1.5 hrs. The reaction mixture was concentrated in vacuo and azeotroped with toluene. Methyl 3-amino-4-fluorobenzoate (1.263 g, 7.47 mmol) (pre-dried at 45° C.) was added followed by pyridine and the mixture was stirred at room temperature under N2 overnight. The reaction mixture was diluted with EtOAc and washed with H2O. The resulting solid was collected by filtration. The filtrate was dried (MgSO4) and concentrated in vacuo and triturated with ether to afford cream solid. The solids were combined and dried at 45° C. to afford the title compound;

Workup

  1. temperatureat reflux for 1.5 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customazeotroped with toluene
  4. washwashed with H2O
  5. filtrationThe resulting solid was collected by filtration
  6. dry with materialThe filtrate was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customtriturated with ether
  9. customto afford cream solid
  10. customdried at 45° C.

Sources & evidence

ORD record
ord-af006b42bb9543278a483ea2c10b41f9
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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