Dimethylformamide → HCID 86620687, compound

HRID 1188514Notes

Reaction equation

HRID 1188514 reaction equation
FC(F)(F)S(O[C:7]1[CH:24]=[CH:23][C:10]2[N:11]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:12]([C:14]([F:17])([F:16])[F:15])=[N:13][C:9]=2[C:8]=1[Cl:25])(=O)=O.[CH3:28][N:29](C=O)C>[C-]#N.[Zn+2].[C-]#N>[Cl:25][C:8]1[C:9]2[N:13]=[C:18]([C:19]([F:22])([F:21])[F:20])[N:11]([CH2:12][C:14]([F:16])([F:17])[F:15])[C:10]=2[CH:23]=[CH:24][C:7]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 57800452HCID 57800452, compound

Product 1

HCID 86620687HCID 86620687, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
140 °C

Procedure

To 4-chloro-1-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-yl trifluoromethanesulfonate (0.053 g, 118 mmol) in DMF (3 mL) was added zinc cyanide (0.008 g, 0.071 mmol) and palladium tetrakistriphenylphosphine (0.014 g, 0.012 mmol). The resulting mixture was heated over night under N2 atm at 140° C. The cooled reaction mixture was partitioned between EtOAc and water, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.0045 g): MS (ESI) m/z 328 (M+1).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between EtOAc and water
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-3f7054f5e6cd42b7879f4d537466f4b7
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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