Aluminium lithium hydride → HCID 68839509, compound

To a solution of 4-(pyridin-3-ylsulfamoylmethyl)benzoic acid methyl ester (1.91 g, 6.23 mmol) in THF (60 mL) at 0° C. was added a 1 M solution of LiAlH4 in THF (13.7 mL, 13.7 mmol), and the mixture was warmed to room temperature. After stirring for 10 minutes, the mixture was heated to reflux temperature for 3 hours. The reaction mixture was cooled to 0° C. and quenched with saturated Na2SO4 aqueous solution (1.9 mL). The mixture was neutralized with 1 N HCl solution (13.7 mL), and then THF was evaporated under reduced pressure. The residue was diluted with water (70 mL) and extracted with CHCl3 (50 mL×3). The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by MPLC on silica gel (6% MeOH in EtOAc) to afford the titled compound (1.43 g, 83%) as a pale yellow solid.

1. temperaturethe mixture was heated
2. temperatureto reflux temperature for 3 hours
3. temperatureThe reaction mixture was cooled to 0° C.
4. customquenched with saturated Na2SO4 aqueous solution (1.9 mL)
5. customTHF was evaporated under reduced pressure
6. additionThe residue was diluted with water (70 mL)
7. extractionextracted with CHCl3 (50 mL×3)
8. washThe organic layer was washed with brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by MPLC on silica gel (6% MeOH in EtOAc)

ORD record

ord-b3e1785858934521bf54e2a082e6e3aa

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495022B2