Diisopropylamine → HCID 86658477, compound

Temperature

0 °C

n-Butyllithium, 2.5 M (44.8 mL, 112 mmol) was added slowly to a solution of diisopropylamine (19.16 mL, 134 mmol) in THF (400 mL) at −78° C. The resulting solution was stirred at 0° C. for 15 minutes before cooling to −78° C. A solution of 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethyl-3-fluorobenzamide (30 g, 74.7 mmol) in THF (400 mL), cooled to −78° C., was added dropwise via cannula under positive pressure. The resulting solution was stirred 3 hours at −78° C. before being quenched with saturated ammonium chloride (200 mL). The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×250 mL). The combined organic extracts were washed with saturated aqueous ammonium chloride, water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to provide an off white solid that was triturated with methanol. The derived solid was dried under a stream of nitrogen to provide 7-bromo-3-chloro-9-fluoro-5H-chromeno[2,3-c]pyridin-5-one. MS m/z=330.1 [M+H].

1. temperaturebefore cooling to −78° C
2. additionwas added dropwise via cannula under positive pressure
3. stirringThe resulting solution was stirred 3 hours at −78° C.
4. custombefore being quenched with saturated ammonium chloride (200 mL)
5. additionThe reaction mixture was diluted with water (20 mL)
6. extractionextracted with EtOAc (3×250 mL)
7. washThe combined organic extracts were washed with saturated aqueous ammonium chloride, water, saturated aqueous sodium chloride
8. dry with materialdried over sodium sulfate
9. filtrationThe solution was filtered
10. concentrationconcentrated in vacuo
11. customto provide an off white solid
12. customthat was triturated with methanol
13. customThe derived solid was dried under a stream of nitrogen

ORD record

ord-a3fc71ef651f4c2896714cae1ac06596

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883782B2