Cesium fluoride → HCID 59466567, compound

A solution (0.52 M) of 2-bromo-5-formylthiazole (1.0 eq.) and CsF (0.2 eq.) in DME was treated with CF3SiMe3 (2.0 eq.) and then stirred for 2 h at RT. The reaction mixture was quenched by adding water and stirred for 15 min. Then, it was diluted with EtOAc and the organic phase was separated. The aqueous phase was extracted twice with EtOAc. The combined organic phase was dried (Na2SO4) and solvents were removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 5-25% EtOAc/petroleum ether to afford the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3, 300K) δ 4.04 (1H, d, J=5.9 Hz), 5.32 (1H, dq, J=5.9 Hz, J=5.9 Hz), 7.59 (1H, s). MS (ES+) C5H3BrF3NOS requires: 261/263, found: 262/264 (M+H)+.

1. customThe reaction mixture was quenched
2. additionby adding water
3. stirringstirred for 15 min
4. additionThen, it was diluted with EtOAc
5. customthe organic phase was separated
6. extractionThe aqueous phase was extracted twice with EtOAc
7. dry with materialThe combined organic phase was dried (Na2SO4) and solvents
8. customwere removed under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel eluting with 5-25% EtOAc/petroleum ether

ORD record

ord-bc3faffa3b0449b0bc7d2aadc60089df

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799825B2