Methanol → 5-Cyanothiophene-2-sulfonamide

A mixture of 5-bromothiophene-2-sulfonamide (0.50 g, 2.1 mmol), zinc cyanide (0.25 g, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.072 g, 0.06 mmol) in dimethylformamide (5 mL, anhydrous) is placed under microwave radiation (under nitrogen atmosphere, 160° C.) for 15 min. Thin layer chromatography (5% methyl alcohol in methylene chloride) demonstrates the reaction is incomplete. Additional tetrakis-(triphenylphosphine)palladium(0) (0.24 g, 0.2 mmol) and dimethylformamide (10 mL) are added to the reaction mixture and placed under microwave radiation (under nitrogen atmosphere at 160° C.) for 37 min. 10 mL of water and 20 mL of ethyl acetate are added to the reaction mixture. The organic phase is separated and the aqueous layer is extracted with 20 mL ethyl acetate. The combined organic layers are dried over sodium sulfate, concentrated in vacuo, and then chromatographed on silica (0–5% methyl alcohol in methylene chloride) to give the title compound, as a white solid (0.22 g, 57% yield).

1. waitplaced under microwave radiation (under nitrogen atmosphere at 160° C.) for 37 min
2. customThe organic phase is separated
3. extractionthe aqueous layer is extracted with 20 mL ethyl acetate
4. dry with materialThe combined organic layers are dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customchromatographed on silica (0–5% methyl alcohol in methylene chloride)

ORD-Eintrag

ord-c726936bb48143acb2070697d2b01b54

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07084170B2