Reacción #1978434

Ecuación de reacción

Sodium hydride

3-bromopropane

6-bromo-3,4-dihydroisoquinolin-1(2H)-one

6-Bromo-3,4-dihydroisoquinolin-1(2H)-one

→

6-bromo-2-propyl-3,4-dihydroisoquinolin-1(2H)-one

Rendimiento 71.1%

6-Bromo-2-propyl-3,4-dihydroisoquinolin-1(2H)-one

Rendimiento 71.1%

Disolventes

DMF

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONOnce addition
2. 2
   Temperaturathen heated at 60° C. for 4hrs
3. 3
   TemperaturaThe reaction mixture was cooled
4. 4
   Otroquenched with water
5. 5
   Extracciónextracted three times with diethyl ether
6. 6
   LavadoThe combined organics were washed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Otroevaporated to dryness
9. 9
   OtroThe residue was purified on silica eluting with 30-100% EtOAc/heptane

Procedimiento

Sodium hydride (60% w/w suspension in oil) (1.17 mmol, 46.7 mg) was suspended in DMF (0.5 ml) under argon. The mixture was cooled to 0° C. before dropwise addition of 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (1K2) (1.06 mmol, 240 mg) in DMF (1.5 ml) The reaction was stirred at 0° C. for 30 min before addition of 3-bromopropane (1K3) (1.592 mmol, 196 mg) in DMF (1 ml). Once addition was complete the reaction was allowed to warm to room temperature then heated at 60° C. for 4hrs. The reaction mixture was cooled, quenched with water and extracted three times with diethyl ether. The combined organics were washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified on silica eluting with 30-100% EtOAc/heptane to give 6-bromo-2-propyl-3,4-dihydroisoquinolin-1(2H)-one (1K4) 202 mg (70.9%); 1H NMR (400 MHz, CDCl3) δ 7.94 (d, 1H) 7.47 (d, 1H) 7.33 (s, 1H) 3.54 (m, 4H) 2.96 (t, 2H) 1.65 (m, 2H) 0.96 (t, 3H).

Fuente