3-Bromo-2-methyl-1-propene → HCID 23729502, compound

HRID 2273277Notes

Reaction equation

HRID 2273277 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.Br[CH2:19][C:20]([CH3:22])=[CH2:21].[In]>C1COCC1.O.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])([CH2:21][C:20]([CH3:22])=[CH2:19])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

7

Reactant 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 5359967IndiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 23729502HCID 23729502, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (609 mg) in THF (4 mL) and H2O (12 mL) at room temperature were added 3-bromo-2-methyl-propene (0.31 mL), followed by indium powder (279 mg, −100 mesh). The resulting mixture was then stirred at room temperature for 18 hr. The resulting mixture was filtered through a pad of Celite®, rinsed with EtOAc, the layers separated, the aqueous layer 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 an orange gum. The orange gum was dissolved in a minimal amount of CH2Cl2 and triturated with hexanes to yield the title compound as an orange solid.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. washrinsed with EtOAc
  3. customthe layers separated
  4. extractionthe aqueous layer extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a residue
  9. customThe residue was purified by flash chromatography with Biotage 40s+ column and elution with 10%-40% EtOAc/hexanes
  10. customto yield an orange gum
  11. customtriturated with hexanes

Sources & evidence

ORD record
ord-fea109ab07d54c8a9b58af5bc0995913
Source dataset
uspto-grants-2015_09
Patent number
US09120830B2

Reaction notes

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