Trifluoroacetic acid → HCID 44199081, compound

HRID 1516612Notes

Reaction equation

HRID 1516612 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:14]1[N:18](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=[N:16][CH:15]=1)O.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl>[F:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:14]1[NH:18][CH:17]=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 67103526HCID 67103526, compound2×

Product 1

HCID 44199081HCID 44199081, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-fluoro-3-(trifluoromethyl)phenyl)(phenyl)(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 8) (2.02 g, 3.49 mmol) in dichloromethane (30 mL) was reacted with TFA: trifluoroacetic acid (5.3 mL, 68 mmol)) and triethylsilane (TES) (2.8 mL, 17 mmol) at room temperature for 24 hours. The mixture was evaporated under reduced pressure and quenched with solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to yield 5-((2-fluoro-3-(trifluoromethyl)phenyl)(phenyl)methyl)-1H-imidazole 700 mg (62%). 1HNMR (CD3OD, 300 MHz): δ 7.54 (s, 1H), 7.52-7.26 (m, 3H), 7.18-7.11 (m, 4H), 6.66 (s, 1H), 5.84 (s, 1H), 5.49 (s, 1H).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customquenched with solid NaHCO3
  3. customthe residue was purified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-9e2f1ffe86ae414a80134fa6f7612b2a
Source dataset
uspto-grants-2012_07
Patent number
US08227499B2

Reaction notes

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