Diethylamine → HCID 86658475, compound

(N,N,N′,N′-tetramethyl-o-(1H-benzotriazol-1-yl)uronium tetrafluoroborate (53.1 g, 165 mmol) was added to a solution of 5-bromo-2-(6-chloropyridin-3-yloxy)-3-fluorobenzoic acid (38.2 g, 110 mmol) and diethylamine (63.3 mL, 606 mmol) in CH2Cl2 (500 mL) at 0° C. After stirring 5 hours at RT, the reaction was quenched with saturated aqueous sodium bicarbonate (250 mL) at RT and diluted with water (100 mL) and the organics was removed in vacuo. The mixture was diluted with EtOAc (250 mL) and the layers were separated and the aqueous layer was extracted with EtOAc (3×100 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate, water, 1N HCl, water, brine, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to provide a residue that was purified by filtering through a pad of silica gel by eluting with 1:2 EtOAc in hexane to provide 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethyl-3-fluorobenzamide.

1. customthe reaction was quenched with saturated aqueous sodium bicarbonate (250 mL) at RT
2. additiondiluted with water (100 mL)
3. customthe organics was removed in vacuo
4. additionThe mixture was diluted with EtOAc (250 mL)
5. customthe layers were separated
6. extractionthe aqueous layer was extracted with EtOAc (3×100 mL)
7. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate, water, 1N HCl, water, brine
8. dry with materialdried over sodium sulfate
9. filtrationThe solution was filtered
10. concentrationconcentrated in vacuo
11. customto provide a residue that
12. customwas purified
13. filtrationby filtering through a pad of silica gel
14. washby eluting with 1:2 EtOAc in hexane

ORD record

ord-6647e998ef0b4d86b54d9858f3f6337e

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883782B2