Reaktion #159021

Reaktionsgleichung

K2CO3

2-(5-{4-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-1-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

2-(5-Bromo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

→

pyrrolidine-1-carboxylic acid tert-butyl ester

Ausbeute 87.3%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegassed with bubbling N2 for 12 min
2. 2
   Temperaturthen cooled to RT
3. 3
   workup.ADDITIONdiluted with ethyl acetate (50 mL)
4. 4
   Waschenwashed with water and brine
5. 5
   TrocknenThe organic phase was dried over magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude residue was purified by silica column chromatography (80% to 100% EtOAc/hexanes)

Vorschrift

2-(5-{4-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-1-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (159 mg, 0.281 mmol), 2-(5-Bromo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (178 mg (0.562 mmol), Pd(PPh3)4 (65 mg, 0.0562 mmol) and K2CO3 (0.281 mL of a 2 M aqueous solution, 0.562 mmol) were combined in 1,2-dimethoxyethane (3 mL) and degassed with bubbling N2 for 12 min. The mixture was then heated to 85° C. for 22 hours then cooled to RT, diluted with ethyl acetate (50 mL) and washed with water and brine. The organic phase was dried over magnesium sulfate and concentrated. The crude residue was purified by silica column chromatography (80% to 100% EtOAc/hexanes) to afford 2-(5-{4-[5-(1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester)-naphthalen-1-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (42 mg, 22%).

Quelle