1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone → Jnj-37654032

HRID 2273271Notes

Reaction equation

HRID 2273271 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.[CH:18]([Mg]Br)=[CH2:19]>C1COCC1.C(Cl)Cl>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]([OH:14])([CH:18]=[CH2:19])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

5

Reactant 2

HCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanoneHCID 178418507HCID 178418507, compound

Product 1

HCID 23729483Jnj-37654032

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (326 mg) in THF (10 mL) −78° C. was added vinyl magnesium bromide (2.42 mL of 1.0 M in THF) dropwise. The resulting mixture was then stirred at 0° C. for 2 hr. The resulting mixture was quenched with H2O and 1 N HCl, extracted with EtOAc, dried over Na2SO4, filtered, and concentrated to yield a residue. The residue was purified by flash chromatography with Biotage 40s+ column and elution with 10%-40% EtOAc/hexanes to yield a yellow gum. The yellow gum was dissolved in a minimal amount of CH2Cl2 and triturated with hexanes to yield the title compound as a light yellow solid.

Workup

  1. customThe resulting mixture was quenched with H2O and 1 N HCl
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a residue
  7. customThe residue was purified by flash chromatography with Biotage 40s+ column and elution with 10%-40% EtOAc/hexanes
  8. customto yield a yellow gum
  9. customtriturated with hexanes

Sources & evidence

ORD record
ord-6be6302ba988489abc5b3c15462036c9
Source dataset
uspto-grants-2015_09
Patent number
US09120830B2

Reaction notes

Loading…