Sodium borohydride → HCID 68182333, compound

To a stirred solution of 6-methyl-2-(methylamino)quinoline-3-carbaldehyde MDE 32036 (134 mg, 0.67 mmol) in THF (10 mL) at 0° C. in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (25 mg, 0.66 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 6 N aq. HCl solution (0.45 mL). After stirring for 15 min at +4° C., the mixture was basified with a 2 N aq. NaOH solution (1.35 mL). THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (50 mL), washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) provided, after evaporation and drying, 6-methyl-2-(methylamino)quinolin-3-yl)methanol MDE32060 as a white solid (73 mg, 55% yield).

1. temperaturethen cooled in an ice bath
2. custombefore quenching by addition of a 6 N aq. HCl solution (0.45 mL)
3. stirringAfter stirring for 15 min at +4° C.
4. customTHF was then removed at 40° C. under vacuum
5. extractionthe solution was extracted with CH2Cl2 (50 mL)
6. washwashed with brine (10 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)
11. customprovided
12. customafter evaporation
13. customdrying

ORD record

ord-6e1d136c2203479e8793077e2acc6d85

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2