反応 #1116918

反応方程式

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

1-methyl-2-pyrrolidinone

sodium bicarbonate

4-chloro-3-fluoro pyridine hydrochloride

→

desired product

収率 60.5%

1-[(3-Fluoro-4-pyridinyl)amino]-3-methyl-5-(phenylmethoxy)-1H-indole

収率 60.5%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度Upon cooling to room temperature
2. 2
   その他The layers were separated
3. 3
   抽出the aqueous phase was extracted with EtOAc (3x)
4. 4
   洗浄The combined organic layers were washed successively with water (2x) and brine (1x)
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過Filtration and concentration
7. 7
   その他gave the crude product
8. 8
   その他Purification via flash column chromatography (silica gel, 50% ethyl acetate/dichloromethane)

実験手順

To a solution consisting of 3-methyl-5-(phenylmethoxy)-1H-indol-1-amine (4.81 g) and 1-methyl-2-pyrrolidinone (83 ml) was added 4-chloro-3-fluoro pyridine hydrochloride (3.20 g). The resulting mixture was heated at 80° C. for 2 hours. Upon cooling to room temperature, dilute aqueous sodium bicarbonate and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous phase was extracted with EtOAc (3x). The combined organic layers were washed successively with water (2x) and brine (1x), and thereafter dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, 50% ethyl acetate/dichloromethane) afforded 4.0 g of the desired product as a solid, m.p. 210°-213° C.

出典