反応 #1116912

反応方程式

3-methyl-5-(phenylmethoxy)-1H-indol-1-amine

4-chloropyridine hydrochloride

4-chloropyridine hydrochloride

sodium bicarbonate

→

desired product

収率 91.7%

3-Methyl-5-(phenylmethoxy)-1-(4-pyridinylamino)-1H-indole

収率 91.7%

溶媒

1-methyl-2-pyrrolidinone

反応条件

後処理

1. 1
   その他Another batch of reaction
2. 2
   その他The above reaction mixtures
3. 3
   抽出extracted with EtOAc (4×) and ether (1×)
4. 4
   洗浄The combined organic layers were washed with water and brine
5. 5
   乾燥by drying (K2CO3)
6. 6
   ろ過Filtration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether/0-5% MeOH)

実験手順

To a solution consisting of 3-methyl-5-(phenylmethoxy)-1H-indol-1-amine (6.31 g) and 1-methyl-2-pyrrolidinone (109 ml) was added 4-chloropyridine hydrochloride (3.94 g). The resulting mixture was heated at 80° C. for 4-5 hours. Another batch of reaction was also carried out with the amine (2.94 g) and 4-chloropyridine hydrochloride (1.84 g) in nmp (50 ml) at 80° C. for 4 hours. The above reaction mixtures were poured together into dilute aqueous sodium bicarbonate and extracted with EtOAc (4×) and ether (1×). The combined organic layers were washed with water and brine followed by drying (K2CO3). Filtration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether/0-5% MeOH) afforded 7.55 g of the desired product. Recrystallization from EtOAc gave a solid, m.p. 167.5°-169.5° C.

出典