Water → 5-Bromo-3-(2-pyrrolidinylethyl)-1-(p-toluene-sulfonyl)-indole

To a solution of 5-bromo-3-(2-pyrrolidinylethyl)-1H-indole (Example 2, 9.10 g, 31 mmol) in tetrahydrofuran (100 mL) cooled to 0° C., were added sodium hydride (12.4 g, 310 mmol) and p-toluenesulfonyl chloride (6.10 g, 32 mmol). The resulting mixture was stirred at room temperature for 3 h, poured into water (200 mL) and extracted into ethyl acetate (200 mL). The organic phase was washed with water (200 mL) and then poured onto a silica gel column which was eluted with ethyl acetate followed by methanol. The title compound was obtained as a yellow syrup (11.7 g, 90%).

1. extractionextracted into ethyl acetate (200 mL)
2. washThe organic phase was washed with water (200 mL)
3. additionpoured onto a silica gel column which
4. washwas eluted with ethyl acetate

ORD record

ord-18dc730b549a4402abb2aa7a12f278c5

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05856510