Diisopropylethylamine → 6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide

To a suspension of 0.10 g (0.40 mmol) 6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-carboxylic acid in 4 ml dicloromethane were added dropwise at 0° C. under argon 0.05 ml (0.6 mmol) oxalyl chloride and one drop of DMF. The reaction mixture was allowed to slowly warm to room temperature. After 1 h the mixture was concentrated in vacuo and redissolved in 2 ml dichloromethane. This solution was added dropwise at 0° C. to a mixture of 0.16 g (0.60 mmol) (3,5-bis-trifluoromethyl-benzyl)-methyl-amine and 0.14 ml (0.80 mmol) N,N-diisopropylethylamine in 2 ml dichloromethane. After 30 min. the reaction mixture was diluted with ethyl acetate and washed with a 1 M aqueous sodium hydroxide solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give 0.29 g of crude product. Flash chromatography gave 0.21 g (quant.) of the title compound.

1. additionwere added dropwise at 0° C. under argon 0.05 ml (0.6 mmol) oxalyl chloride
2. concentrationAfter 1 h the mixture was concentrated in vacuo
3. dissolutionredissolved in 2 ml dichloromethane
4. washwashed with a 1 M aqueous sodium hydroxide solution
5. extractionThe aqueous layer was extracted with ethyl acetate
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customto give 0.29 g of crude product

ORD record

ord-ce746721c5dc4ef69779611a11a74668

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176205B2