3,5-Bis(trifluoromethyl)benzoyl chloride → N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Temperatur

-78 °C

To a solution of (4-bromo-pyridin-3-yl)-methyl-amine (1 g, 5.376 mmol) in THF (8 mL) was added LiHMDS (1M solution in THF, 10.7 mL, 10.7 mmol, CAS RN 4039-32-1) dropwise at −78° C., and stirred for 15 minutes before 3,5-bis-trifluoromethyl-benzoyl chloride (1.5 mL, 8.06 mmol, CAS RN 785-56-8) was added to the reaction mixture. After stirring at −78° C. for 1 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (10 mL) and diluted with EtOAc (40 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, filtered, and evaporated off in vacuo. The residue was purified by column chromatography over silica gel (15% EtOAc in n-hexane) to afford the title compound. Pale yellow solid (985 mg, 43%). MS (ESI): m/z=427.2 [M+H]+.

1. additionwas added to the reaction mixture
2. customwas quenched with saturated aqueous NH4Cl solution (10 mL)
3. additiondiluted with EtOAc (40 mL)
4. washThe combined organic layers were washed with brine (15 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated off in vacuo
8. customThe residue was purified by column chromatography over silica gel (15% EtOAc in n-hexane)

ORD-Eintrag

ord-c62f8483bb5a462889152995cac312b1

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08987307B2