Iodine → HCID 44443106, compound

HRID 2273290Notes

Reaction equation

HRID 2273290 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[C:19](=[C:21]([CH3:23])[CH3:22])[CH3:20].II.[Mg]>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])([C:19]([CH3:20])=[C:21]([CH3:23])[CH3:22])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

7

Reactant 4

HCID 807IodineHCID 5204672-Bromo-3-methyl-2-buteneHCID 5462224MagnesiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 44443106HCID 44443106, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (577 mg) in THF (5 mL) at 0° C. was added Grignard reagent, which was freshly prepared from 2-bromo-3-methyl-2-butene (1.73 mL), a small iodine flake, and magnesium powder (347 mg) in THF (5 mL). The resulting mixture was stirred at room temperature for 3 hr. The reaction was quenched with NH4Cl (sat. aq), filtered through a pad of Celite®, rinsed with EtOAc, the layers were 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 a yellow solid. The yellow solid was dissolved in a minimal amount of CH2Cl2 and triturated with hexanes to yield the title compound as an off-white solid.

Workup

  1. customThe reaction was quenched with NH4Cl (sat. aq)
  2. filtrationfiltered through a pad of Celite®
  3. washrinsed with EtOAc
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a residue
  10. customThe residue was purified by flash chromatography with Biotage 40s+ column and elution with 10%-40% EtOAc/hexanes
  11. customto yield a yellow solid
  12. customtriturated with hexanes

Sources & evidence

ORD record
ord-8a0ca1b3adf34cbcb67d5618ccbf718b
Source dataset
uspto-grants-2015_09
Patent number
US09120830B2

Reaction notes

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