Triethylamine → 5-Bromo-2-methylthiazole-4-carbonitrile

5-Bromo-2-methyl-thiazole-4-carboxylic acid amide (11.3 g, 51.1 mmol) was dissolved in 150 ml dichloromethane and triethylamine (14.2 ml, 102.2 mmol) was added. Trifluoroaceticanhydride (14.3 ml, 102.2 mmol) was added dropwise at 0° C. and the mixture stirred without cooling for 2 hrs. The reaction mixture was quenched with saturated NaHCO3-solution and extracted with ethyl acetate. The organic extract was washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->20:80 gradient). The desired compound was obtained as a light yellow solid (6.4 g, 62%), MS: m/e=204.0 (M+H+).

1. temperaturewithout cooling for 2 hrs
2. customThe reaction mixture was quenched with saturated NaHCO3-solution
3. extractionextracted with ethyl acetate
4. extractionThe organic extract
5. washwas washed with brine
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->20:80 gradient)

ORD record

ord-ef1297d2f19143f3b6ff2a6a26a94ed0

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659401B2