Реакция #1978434

Уравнение реакции

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

Выход 71.1%

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

Выход 71.1%

Растворители

DMF

DMF

DMF

Условия реакции

Обработка

1. 1
   workup.ADDITIONOnce addition
2. 2
   Температураthen heated at 60° C. for 4hrs
3. 3
   ТемператураThe reaction mixture was cooled
4. 4
   Другоеquenched with water
5. 5
   Экстракцияextracted three times with diethyl ether
6. 6
   ПромывкаThe combined organics were washed with brine
7. 7
   Сушкаdried (MgSO4)
8. 8
   Другоеevaporated to dryness
9. 9
   ДругоеThe residue was purified on silica eluting with 30-100% EtOAc/heptane

Методика

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).

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