Ethyl bromopyruvate → Ethyl 2-(trifluoromethyl)-1,3-thiazole-4-carboxylate

A mixture of 2,2,2-trifluoroacetamide (7.12 g, 63 mmol) and Lawesson's reagent (15.3 g, 37.8 mmol) in THF (60 mL) was heated at reflux for 18 hours. The reaction was then cooled down to RT and treated with ethyl bromopyruvate (8.0 mL, 63 mmol). The reaction was stirred at reflux for an additional 18 hours, then concentrated under vacuum and diluted with ethyl acetate. This mixture was washed with water (1×) and brine (1×), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (8×11 cm, toluene, then second time with 120 g silica gel, hexane/ethyl acetate) to give the title material (4.47 g, 32%) as a pale yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.37 (s, 1H), 4.45 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 1H).

1. temperaturewas heated
2. temperatureat reflux for 18 hours
3. temperatureat reflux for an additional 18 hours
4. concentrationconcentrated under vacuum
5. additiondiluted with ethyl acetate
6. washThis mixture was washed with water (1×) and brine (1×)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by silica gel chromatography (8×11 cm, toluene

ORD-Eintrag

ord-8c343e64119149669e4139319da55b29

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08927688B2