Réaction #1962335

Équation de réaction

4-chloro-N-({4-chloro-3-[(3-chloro-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

TFA

→

4-chloro-N-({4-chloro-3-[(3-chloro-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide

Rendement 57.0%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched with saturated sodium bicarbonate
2. 2
   Autrethe organic layer was separated
3. 3
   AutreThe solvent was removed
4. 4
   Autrethe crude material was purified via silica gel chromatography

Mode opératoire

To a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (64 mg, 0.112 mmol) in DCM (5 ml) was added TFA (2.0 ml) and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched with saturated sodium bicarbonate and the organic layer was separated. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-chloro-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (28 mg, 0.063 mmol, 57% yield). 1H NMR (400 MHz, DMSO-d5) δ ppm 12.83-13.43 (m, 1H), 8.20 (d, 1H), 7.73 (s, 1H), 7.44 (d, 1H), 7.29 (t, 1H), 7.01 (s, 1H), 6.73 (s, 1H), 6.66 (s, 1H), 4.48 (d, 2H), 2.53 (q, 2H), 1.08 (t, 3H). LC-MS (ES+) m/z 441.59, [M+H].

Source