Реакция #48316

Уравнение реакции

6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinolin-4-amine

tetrahydrofuran

neopentylmagnesium chloride

→

desired product

2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amine

Условия реакции

Обработка

1. 1
   ДругоеThe reaction vessel was sealed
2. 2
   Температураheated to 65 deg C
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 6 hours
4. 4
   ФильтрацияThe crude mixture was filtered through a plug of celite with EtOAc
5. 5
   Концентрированиеconcentrated in the presence of silica gel
6. 6
   ДругоеThe crude mixture was purified with the MPLC (100% DCM to 100% 90:10:1 DCM:MeOH:NH4OH)

Методика

To neopentylmagnesium chloride (1.65 ml, 1.65 mmol) was added zinc(II) chloride (2.19 ml, 1.10 mmol) dropwise—strong exotherm was observed. The resulting mixture stirred for 10 minutes. A solution of 6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinolin-4-amine (0.0700 g, 0.274 mmol) in tetrahydrofuran (1.37 ml, 0.274 mmol) was then added followed by palladium tetrakistriphenylphosphine (0.0317 g, 0.0274 mmol). The reaction vessel was sealed and heated to 65 deg C. The reaction mixture was stirred for 6 hours. The crude mixture was filtered through a plug of celite with EtOAc and concentrated in the presence of silica gel. The crude mixture was purified with the MPLC (100% DCM to 100% 90:10:1 DCM:MeOH:NH4OH) to provide the desired product. MS m/z: 230 (M−NH2).

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