Acetonitrile → HCID 44443103, compound

HRID 2273273Notes

Reaction equation

HRID 2273273 reaction equation
[C:1](#[N:3])[CH3:2].[Li]CCCC.[Cl:9][C:10]1[C:24]([Cl:25])=[CH:23][C:13]2[NH:14][C:15]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[N:16][C:12]=2[CH:11]=1>C1COCC1>[Cl:25][C:24]1[C:10]([Cl:9])=[CH:11][C:12]2[NH:16][C:15]([C:17]([OH:22])([C:18]([F:21])([F:19])[F:20])[CH2:2][C:1]#[N:3])=[N:14][C:13]=2[CH:23]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanoneHCID 178418339Butyllithium

Product 1

HCID 44443103HCID 44443103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of dry acetonitrile (0.4 mL) in THF (10 mL) at −78° C. was added n-BuLi (2.9 mL of 2.5 M in hexanes). The resulting mixture was stirred for 45 min. at −78° C. To the solution was then added a solution of 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (930 mg) in THF (5 mL). The resulting mixture was stirred at −78° C. for 1 hr. The reaction was quenched with NH4Cl (aq) and the resulting mixture extracted with EtOAc. The combined extracts were washed with brine and dried over Na2SO4. The resulting crude material was purified by column chromatography (SiO2; 0-15% ethyl acetate/hexanes) to yield the title compound as a yellow solid.

Workup

  1. stirringThe resulting mixture was stirred at −78° C. for 1 hr
  2. customThe reaction was quenched with NH4Cl (aq)
  3. extractionthe resulting mixture extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe resulting crude material was purified by column chromatography (SiO2; 0-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8a97ecef82fb443db13937245006fbd3
Source dataset
uspto-grants-2015_09
Patent number
US09120830B2

Reaction notes

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