반응 #45393

반응 방정식

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

용매

ethyl acetate

반응 조건

후처리

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

실험 절차

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.

출처