Indole-3-Carboxaldehyde → HCID 13979912, compound

To a solution of 1H-indole-3-carboxaldehyde (300 mg, 2.07 mmol) in 4.1 mL of dry dimethylsulfoxide was added sodium hydride (108 mg, 55%, 2.5 mmol) under nitrogen at 0° C. After the reaction mixture was stirred for 30 min, methylsulfonyl chloride (0.19 mL, 2.5 mmol) was added with additional stirring for 1 h. The reaction mixture was diluted with 10 mL of ethyl acetate and 10 mL of saturated NH4Cl aqueous solution at 0° C., successively, and the solution was extracted with 100 mL of ethyl acetate. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the solution was concentrated in vacuo. The residue was purified by recrystallization (chloroform/hexane) to obtain the title compound as a pale red solid (300 mg, 65%).

1. stirringwith additional stirring for 1 h
2. extractionsuccessively, and the solution was extracted with 100 mL of ethyl acetate
3. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
4. dry with materialdried over MgSO4
5. filtrationAfter filtration
6. concentrationthe solution was concentrated in vacuo
7. customThe residue was purified by recrystallization (chloroform/hexane)

ORD record

ord-78b62b6adb0c4affaafc71937ae2e557

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962674B2