Reaction #158901

Reaction equation

(1-{4,4-difluoro-2-[5-(4-trimethylsilanylethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

K2CO3

→

(1-{2-[5-(4-ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Yield 100.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Filtrationthe reaction was filtered
2. 2
   Concentrationthen concentrated
3. 3
   workup.ADDITIONThe residue was diluted with EtOAc
4. 4
   Washthen washed with H2O
5. 5
   ExtractionThe aqueous phase was back-extracted with EtOAc two times
6. 6
   Washwashed with brine
7. 7
   Dryingdried over Na2SO4
8. 8
   Concentrationconcentrated
9. 9
   OtherThe crude material was purified by silica gel chromatography (20-80% EtOAc-hexanes gradient)

Procedure

To (1-{4,4-difluoro-2-[5-(4-trimethylsilanylethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (412 mg, 0.82 mmol) in MeOH (8 mL) was added K2CO3 (227 mg, 1.64 mmol). After stirring for 5 h, the reaction was filtered then concentrated. The residue was diluted with EtOAc then washed with H2O. The aqueous phase was back-extracted with EtOAc two times then the organic phases were combined, washed with brine, dried over Na2SO4, and concentrated. The crude material was purified by silica gel chromatography (20-80% EtOAc-hexanes gradient) to afford (1-{2-[5-(4-ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (371 mg, 0.82 mmol, quantitative yield). LCMS-ESI+: calc'd for C22H25F2N4O3: 431.2 (M+H+). Found: 431.1 (M+H+).

Source