Methylamine hydrochloride → 3-(1H-Indol-6-yl)-3-(2-methoxy-phenyl)-N-methyl-propionamide

To a 5° C. stirring suspension of MeNH2—HCl (160 mg, 2.4 mmol) in benzene (2 ml) under N2, in a sealed tube was added dropwise Me3Al (2M in toluene, 1.2 ml, 2.4 mmol). The mixture was stirred at room temperature for 1 hour and a solution of 3-(1H-Indol-6-yl)-3-(2-methoxy-phenyl)-propionic acid methyl ester XXXVII (340 mg, 1.1 mmol) in benzene (10 ml) was added. The resulting mixture was stirred at 90° C. for about 4.5 hours, cooled to room temperature, and the reaction was quenched by slowly adding HCl (1M, 25 ml). The resulting mixture was stirred for 10 minutes, diluted with H2O, and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and evaporated to provide 3-(1H-indol-6-yl)-3-(2-methoxy-phenyl)-N-methyl-propionamide XXXVIII (320 mg, 94% yield).

1. stirringThe mixture was stirred at room temperature for 1 hour
2. stirringThe resulting mixture was stirred at 90° C. for about 4.5 hours
3. temperaturecooled to room temperature
4. customthe reaction was quenched by slowly adding HCl (1M, 25 ml)
5. stirringThe resulting mixture was stirred for 10 minutes
6. additiondiluted with H2O
7. extractionextracted with EtOAc
8. washThe organic layer was washed with H2O and brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customevaporated

ORD record

ord-33ee59782410489bb3ce2423ffeb3684

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803830B2