5-Chloropyridine-2-carboxaldehyde → HCID 86707784, compound

HRID 2410141Notes

Reaction equation

HRID 2410141 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1C=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[OH:12])=[O:5])[CH3:2].ClC1C=CC(C=O)=[N:29]C=1>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][N:29]=1)[OH:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 101032675-Chloropyridine-2-carboxaldehydeHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate

Product 1

HCID 86707784HCID 86707784, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was obtained in analogy to the procedure described for intermediate B but using 5-chloro-2-formylpyridine. After completion, the reaction mixture was diluted with EtOAc and extracted with a saturated NaHCO3 solution. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flas chromatography (heptane/EtOAc, 100:0→0:100) to give the title compound. tR: 1.00 min (LC-MS 2); ESI-MS: 402.0/404.0 [M+H]+ (LC-MS 2).

Workup

  1. extractionextracted with a saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flas chromatography (heptane/EtOAc, 100:0→0:100)

Sources & evidence

ORD record
ord-881f02d5606a44de8bcc21c6abf88747
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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