Trifluoroacetic acid → HCID 178509560, compound

HRID 1924873Notes

Reaction equation

HRID 1924873 reaction equation
O[CH:2]([C:17]1[N:18]=[CH:19][N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:20]1[CH:21]=[C:17]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:18]=[CH:19]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 67519624HCID 67519624, compound2×

Product 1

HCID 178509560HCID 178509560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2′-[Hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-biphenyl-4-carbonitrile (Intermediate D2) (2.4 g, 4.6 mmol) in CH2Cl2 (100 mL) was cooled to 0° C. and treated with triethyl silane, Et3SiH (7.4 mL, 46 mmol) (commercially available from Aldrich) followed by trifluoroacetic acid, TFA (10.7 mL, 140 mmol) dropwise. After several minutes the cooling bath was removed and the mixture was stirred at rt for an additional 12 h. The reaction was quenched with solid NaHCO3 followed by aqueous workup. The layers were separated and the organic layers were combined and dried over Na2SO4. The mixture was filtered and concentrated to dryness. The residue was purified by chromatography on silica gel with 3% NH3-MeOH: CH2Cl2 to give the product 2′-(1H-imidazol-4-ylmethyl)-biphenyl-4-carbonitrile (Intermediate D3), 0.74 mg, 62% yield.

Workup

  1. customAfter several minutes the cooling bath was removed
  2. customThe reaction was quenched with solid NaHCO3
  3. customThe layers were separated
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel with 3% NH3-MeOH

Sources & evidence

ORD record
ord-3f41f58d54624b96aa100ad8265f3154
Source dataset
uspto-grants-2012_05
Patent number
US08178571B2

Reaction notes

Loading…