Diethyl Ether → HCID 89439926, compound

Temperature

110 °C

A flask was charged with 5-bromonicotinaldehyde (0.5 g, 2.69 mmol), ethanesulfonamide (0.367 g, 3.36 mmol) and toluene (25 mL), then titanium tetra-isopropoxide (1.53 g, 5.38 mmol) was added dropwise. The reaction mixture was heated to 110° C. over night and then concentrated in vacuo. The residue was dissolved in THF (25 mL) and cooled down to −40° C. A 3 M solution of ethylmagnesium bromide in ether (2.24 mL, 6.72 mmol) was added dropwise at this temperature and the resulting mixture was slowly warmed up to −20° C. and stirred for 2.5 h. The mixture was poured into a saturated NH4Cl solution (15 mL), the resulting suspension was filtered and the filtrate was extracted with DCM (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.5 g, 56%) as light yellow oil. MS: 307.1 and 308.9.

1. concentrationconcentrated in vacuo
2. dissolutionThe residue was dissolved in THF (25 mL)
3. temperaturecooled down to −40° C
4. temperaturethe resulting mixture was slowly warmed up to −20° C.
5. filtrationthe resulting suspension was filtered
6. extractionthe filtrate was extracted with DCM (2×50 mL)
7. dry with materialCombined organics were dried over Na2SO4
8. filtrationfiltered
9. customevaporated to dryness
10. customThe residue was purified by silica gel flash chromatography
11. washeluting with a 0 to 5% MeOH-DCM gradient

ORD record

ord-46d8d4b6f84d432191607858c3ea48d4

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260408B2