Quinoline → HCID 67003517, compound

Temperature

200 °C

To a mixture of quinoline (5 mL) and copper powder (0.39 g, 6.2 mmol) in a sealed tube was added 7-bromo-5-(trifluoromethyl)-1-benzothiophene-2-carboxylic acid (1.0 g, 3.1 mmol). The mixture was heated to 200° C. for 20 minutes, then allowed to cool to room temperature. The mixture was filtered, then the collected precipitate was washed with toluene. The filtrate was concentrated, then the resulting brown oil was diluted with EtOAc and poured into 6.0 M HCl (aq). The layers were separated, then the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 6.0 M HCl (aq), water, then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 0-1% EtOAc/hexanes to afford the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 8.10 (br s, 1H); 7.77 (br s, 1H); 7.69 (d, J=5.5 Hz, 1H); 7.57 (d, J=5.5 Hz, 1H). LC1: 4.02 min. Compound does not ionize.

1. temperatureto cool to room temperature
2. filtrationThe mixture was filtered
3. washthe collected precipitate was washed with toluene
4. concentrationThe filtrate was concentrated
5. additionthe resulting brown oil was diluted with EtOAc
6. additionpoured into 6.0 M HCl (aq)
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with ethyl acetate
9. washThe combined organic layers were washed with 6.0 M HCl (aq), water
10. dry with materialsaturated NaCl (aq), dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by silica gel chromatography
14. washeluting with 0-1% EtOAc/hexanes

ORD record

ord-ade340e2128c4fd8af69d59136d8051a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359339B2