HCID 11551113, compound → 7-Methoxy-3-(6-methoxy-pyridin-3-yl)-4-methyl-2H-chromen-2-ol

A solution of 7-methoxy-3-(6-methoxy-pyridin-3-yl)-4-methyl-chromen-2-one (430 mg, 1.45 mmol, 1 eq) in toluene (5 mL) was cooled to −78° C. in a 100 mL 3-neck round bottom flask under nitrogen. To the reaction mixture was slowly added a toluene solution of diisobutylaluminum hydride (1.5 mL of 1.0 M, mmol, 1.1 eq), with the temperature of the reaction mixture maintained at less than −70° C. The reaction was stirred for 1 hour, quenched with addition of methanol (0.5 mL). The resulting solution was diluted with dichloromethane, the solution washed with a saturated solution of Rochelle salt, then washed with brine, dried on anhydrous sodium sulphate, filtered and evaporated to yield the crude compound as a yellow solid. The solid was purified by column chromatography using a hexane:ethyl acetate mixture (1:1) to yield the title product as a yellow solid.

1. temperaturewith the temperature of the reaction mixture maintained at less than −70° C
2. customquenched with addition of methanol (0.5 mL)
3. additionThe resulting solution was diluted with dichloromethane
4. washthe solution washed with a saturated solution of Rochelle salt
5. washwashed with brine
6. dry with materialdried on anhydrous sodium sulphate
7. filtrationfiltered
8. customevaporated
9. customto yield the crude compound as a yellow solid
10. customThe solid was purified by column chromatography

ORD record

ord-c6772abf8b0241e8920e55a2cd338899

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399767B2