반응 #1590545

반응 방정식

6-bromo-3-iodo-8-methylsulfanyl-imidazo[1,2-a]pyrazine

[4-[(cyclopropylamino)carbonyl]phenyl]-boronic acid

ethyl acetate

tripotassium phosphate

→

4-(6-bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazin-3-yl)-N-cyclopropyl-benzamide

수율 56.3%

용매

THF

water

반응 조건

후처리

1. 1
   기타at rt
2. 2
   세척the organic phase was washed with sat. sodium chloride solution
3. 3
   건조dried over sodium sulphate
4. 4
   여과filtered
5. 5
   기타After removal of the solvent, purification by flash chromatography (n-hexane/ethyl acetate 85:15)

실험 절차

To a stirred solution of intermediate example 3-1 6-bromo-3-iodo-8-methylsulfanyl-imidazo[1,2-a]pyrazine (25.00 g, 67.6 mmol) in THF (214 mL) and water (100 mL) was subsequently added 43 g tripotassium phosphate (203 mmol, 3 eq), 18.01 g [4-[(cyclopropylamino)carbonyl]phenyl]-boronic acid (87.8 mmol, 1.3 eq) and 5.52 g Pd(dppf)Cl2 (6.8 mmol, 0.1 eq) in one portion at rt under argon atmosphere. After stirring overnight at 45° C., ethyl acetate was added and the organic phase was washed with sat. sodium chloride solution, dried over sodium sulphate and filtered. After removal of the solvent, purification by flash chromatography (n-hexane/ethyl acetate 85:15) yielded 15.33 g (56.26%) 4-(6-bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazin-3-yl)-N-cyclopropyl-benzamide: 1H-NMR (300 MHz, CDCl3): δ=8.07 (1H, s), 7.92 (2H, d), 7.77 (1H, s), 7.60 (2H, d), 6.32 (1H, bs), 2.95 (1H, m), 2.70 (3H, s), 0.92 (2H, m), 0.67 (2H, m) ppm. UPLC-MS: RT=1.12 min; m/z 404.3 [MH+]; required MW=403.3.

출처