Dimethylformamide → 2-Chloro-6-methoxypyridine-3-carbaldehyde

The 3-bromo-2-chloro-6-methoxy-pyridine (0.50 g, 2.26 mmol) obtained in (19-1) above was dissolved in toluene (dehydrated) (11 mL), and thereafter, n-butyllithium (1.46 mL, 2.3 mmol, 1.57 mmol/L hexane solution) was added dropwise to the solution at −78° C. in an argon atmosphere. The obtained mixture was stirred at the same temperature as described above for 30 minutes, and DMF (1.0 mL) was then added to the reaction solution. The obtained mixture was further stirred for 30 minutes. Thereafter, a saturated ammonium chloride water (20 mL) was slowly added to the reaction solution, and the temperature of the mixture was then increased to room temperature. The mixture was extracted with diethyl ether (20 mL) twice, and organic layers were gathered. The resultant was dried over anhydrous sodium sulfate and was then filtrated, followed by vacuum concentration. The obtained residue was purified by silica gel column chromatography (SiO2 30 g, hexane:ethyl acetate=95:5 to 80:20), so as to obtain 180 mg of 2-chloro-6-methoxy-3-pyridinecarboxaldehyde.

1. additionwas then added to the reaction solution
2. stirringThe obtained mixture was further stirred for 30 minutes
3. extractionThe mixture was extracted with diethyl ether (20 mL) twice
4. dry with materialThe resultant was dried over anhydrous sodium sulfate
5. filtrationwas then filtrated
6. concentrationfollowed by vacuum concentration
7. customThe obtained residue was purified by silica gel column chromatography (SiO2 30 g, hexane:ethyl acetate=95:5 to 80:20)

ORD record

ord-94e3901d239749a8829f6ebe7111c9ce

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018238B2