Reacción #717702

Ecuación de reacción

1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid

Diisopropylethylamine

2-(1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamido)acetic acid

methyl 2-(methylamino)acetate hydrochloride

TBTU

→

raw product

N-(2-Amino-2-oxoethyl)-1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamide

Disolventes

DMF

—

ice water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with methanol/dichloromethane (5:95; 3×40 mL)
2. 2
   LavadoThe combined organic layers were successively washed with saturated sodium hydrogen carbonate, saturated ammonium chloride solution, and brine
3. 3
   Secadodried over sodium sulfate
4. 4
   Concentraciónconcentrated

Procedimiento

Diisopropylethylamine (0.34 mL, 1.99 mmol), EDCxHCl (0.19 g, 0.992 mmol) and HOBt ammonium salt (0.15 g, 0.997 mmol) were added to 2-(1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamido)acetic acid (0.3 g, 0.66 mmol, synthesized from 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid in three steps comprising a TBTU mediated amide coupling of methyl 2-(methylamino)acetate hydrochloride, the oxidation of the thioether and the hydrolysis of the methyl ester) in DMF (3.0 mL). The reaction mixture was stirred at room temperature for 16 h, diluted with ice water and extracted with methanol/dichloromethane (5:95; 3×40 mL). The combined organic layers were successively washed with saturated sodium hydrogen carbonate, saturated ammonium chloride solution, and brine, dried over sodium sulfate and concentrated to yield the raw product which was purified by column chromatography [silica; methanol/dichloromethane=5:95]. White solid. Yield: 0.13 g (43% of theory)

Fuente