1-Methanesulfonylindoline synthesis

Yield:5825-63-8 96%

Reaction Conditions:

with pyridine at 20;Product distribution / selectivity;

Steps:

20.1

Example 20Synthesis of 5-((4-methoxyphenyl)sulfonyl)-1-(methylsulfonyl)indolineReagents Table MW Reagent/raw material (gr/mole) Quantity moles Indoline 119.16 2 g 16.7 mmol methanesulfonyl chloride 114.55 2.86 g 25 mmol 1-(methylsulfonyl)indoline 197.25 0.5 g 2.5 mmol 4-methoxybenzene-1-sulfonyl 206.65 0.43 g 2.11 mmol chlorideFeCl₃ 126.75 0.8 6.2 mmol Procedure:Synthesis of 1: Indoline was dissolved in 5 ml dry pyridine, and methanesulfonyl chloride was added. Reaction stirred for overnight at RT, intense red color developed. When complete by HPLC and LCMS, solvent was evaporated, crude reaction mixture was dissolved in EA and washed with HCl 1N, water and brine. Organic phase was evaporated and to give 3.05 g product 100% pure, (96% yield)

References:

US2012/108631,2012,A1 Location in patent:Page/Page column 57