Reaktion #45393

Reaktionsgleichung

tert-Butyl-6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate

ethynylcyclohexane

diisopropylamine

N,N-dimethylformamide

ethynylcyclohexane

→

tert-butyl 6-amino-7-(cyclohexylethynyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated for another 60 min
2. 2
   TemperaturThe reaction was cooled
3. 3
   Waschenwashed several times with water
4. 4
   SonstigeThe solvent removed under reduced pressure
5. 5
   Sonstigethe residue was chromatographed on a silica gel column (50%-70% ethyl acetate/hexane)
6. 6
   Sonstigeto give 400 mg of C32.1 as a yellow solid
7. 7
   SonstigeRet time 3.15 min, (M+H)+=384.41

Vorschrift

A1.12 tert-Butyl-6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate (1.0 g, 2.48 mmol), dichlorobis(triphenylphosphine)palladium (75 mg, 0.11 mmol), ethynylcyclohexane (0.3 g, 2.8 mmol), CuI (25 mg, 0.13 mmol), and diisopropylamine (5 mL) were added to N,N-dimethylformamide (7 mL). The reaction mixture was heated at 95° C. (in preheated oil bath) for 60 min. Additional ethynylcyclohexane (0.3 g, 2.8 mmol) was added to the reaction mixture and heated for another 60 min. The reaction was cooled and diluted with ethyl acetate and washed several times with water. The solvent removed under reduced pressure and the residue was chromatographed on a silica gel column (50%-70% ethyl acetate/hexane) to give 400 mg of C32.1 as a yellow solid. LCMS B: Ret time 3.15 min, (M+H)+=384.41.

Quelle