Reacción #2265729

Ecuación de reacción

compound 1-E

tert-Butyl (3-methylimidazo[1,2-a]pyridin-2-yl)carbamate

NaH

Methyl 4-(chlorosulfonyl)benzoate

→

compound 1-F

Rendimiento 60.0%

Methyl 4-(N-(tert-butyoxycarbonyl)-N-(3-methylimidazo[1,2-a]pyridin-2-yl)sulfamoyl)benzoate

Rendimiento 60.0%

Disolventes

DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature for 2 h
2. 2
   Lavadowashed with H2O (2×), brine
3. 3
   Secadodried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Otrothe solvent evaporated under reduced pressure
6. 6
   Otroto afford a crude solid
7. 7
   OtroThe crude material was purified by flash column chromatography (SiO2)
8. 8
   Lavadoeluting with a heptanes-EtOAc gradient

Procedimiento

To a solution of compound 1-E (0.174 g, 0.703 mmol) in DMF (5 mL), cooled to 0° C., was added 60% NaH (0.028 g, 0.703 mmol) and the reaction mixture was stirred at 0° C. for 20 min. Methyl 4-(chlorosulfonyl)benzoate (0.247 g, 1.06 mmol) was added in one-portion and the reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to afford a crude solid. The crude material was purified by flash column chromatography (SiO2) eluting with a heptanes-EtOAc gradient to afford compound 1-F as a white solid (0.188 g, 60%). 1H-NMR (CDCl3): δ 8.22-8.35 (dd, 2H), 7.90-7.92 (d, 1H), 7.61-7.64 (d, 1H), 7.22-7.24 (m, 1H), 6.90-6.93 (m, 1H), 3.98 (s, 3H), 2.55 (s, 3H), 1.32 (s, 9H); MS: m/z 446.1 (MH+).

Fuente