Réaction #636454

Équation de réaction

4-(7-bromo-isoquinoline-1-yl)-piperazine-1-carboxylic acid, tert-butyl ester

3,5-dimethyl-thiophenol

→

title compound

Rendement 65.0%

4-[7-(3,5-Dimethyl-phenylsulfanyl)-isoquinolin-1-yl]-piperazine-1-carboxylic acid tert-butyl ester

Rendement 65.0%

Solvants

nBuOH

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   ConcentrationThe filtrate was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   LavageThe organic phase was washed with water (50 mL×3)
5. 5
   Autreseparated
6. 6
   Séchagedried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   AutreThe volatiles were evaporated
9. 9
   Autrethe residue was purified by flash column chromatography (SiO2, n-pentane:ethyl acetate 9.8:0.2→8:2)

Mode opératoire

A mixture of 4-(7-bromo-isoquinoline-1-yl)-piperazine-1-carboxylic acid, tert-butyl ester (0.5 g, 1.3 mmol), 3,5-dimethyl-thiophenol (180 mg, 1.3 mmol), NatBuO (0.44 g, 4.5 mmol), Pd(PPh3)4 (74 mg, 0.065 mmol) in nBuOH (10 mL) was heated at 110° C., 3 h. The reaction mixture was filtered. The filtrate was concentrated and the residue was dissolved in ethyl acetate. The organic phase was washed with water (50 mL×3), separated and dried (MgSO4), filtered. The volatiles were evaporated and the residue was purified by flash column chromatography (SiO2, n-pentane:ethyl acetate 9.8:0.2→8:2) to give 380 mg of the title compound as colourless oil (yield 65%). 1H NMR (CDCl3) δ 8.05-8.10 (m, 1H), 7.80-7.85 (m. 1H), 7.60-7.75 (m, 1H), 7.17-7.25 (m, 1H), 7.10 (bs, 2H), 7.00 (bs, 1H), 3.40-3.50 (m, 4H), 3.10-3.20 (m, 4H), 2.25 (bs, 6H), 1.50 (s, 9H).

Source