Cesium carbonate → HCID 67206182, compound

Temperature

80 °C

A solution of 2-fluoro-4-hydroxy-benzoic acid (4.0 g, 25.6 mmol) in DMF (250 mL) was added Cs2CO3 (9.2 g, 28.2 mmol) and the reaction mixture was stirred at 80° C. for 1 h prior to the addition of 2-chloro-benzothiazole (3.3 mL, 25.6 mmol). The reaction mixture was stirred at 100° C. for 50 h, then cooled to rt, and the solid was filtered. The filtrate was diluted with EtOAc (200 mL) and water (100 mL), neutralized with 1 M HCl and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×200 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated to afford the title compound as a colorless solid (4.7 g, 63%). MS (ESI): mass calcd. for C14H8FNO3S, 289.0; m/z found, 290.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.21 (t, J=8.5 Hz, 1H), 7.99 (d, J=8.5 Hz, 1H), 7.87 (d, J=8.11 Hz, 1H), 7.63-7.45 (m, 4H).

1. stirringThe reaction mixture was stirred at 100° C. for 50 h
2. temperaturecooled to rt
3. filtrationthe solid was filtered
4. additionThe filtrate was diluted with EtOAc (200 mL) and water (100 mL)
5. customthe organic layer was separated
6. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-519df80ad80e42fab8127fe12325c5ac

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367719B2