Sodium borohydride → HCID 68182175, compound

To a stirred solution of 5-ethoxyquinoline-3-carbaldehyde CCH 29158B (98 mg, 487 μmol) in THF (10 mL) at 0° C. in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (18 mg, 476 μmol) 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 (0.33 mL). After stirring for 15 min at that temperature, the mixture was basified by a 2 N aq. NaOH solution (1.0 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 CH2Cl2:MeOH=100:0 to 97:3) provided 41 mg (5-ethoxyquinolin-3-yl)methanol MDE 32076 as a colorless oil (41 mg, 41% yield).

1. temperaturethen cooled in an ice bath
2. custombefore quenching by addition of a 6 N aq. HCl solution (0.33 mL)
3. stirringAfter stirring for 15 min at that temperature
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 CH2Cl2:MeOH=100:0 to 97:3)

ORD record

ord-914630b46dac4306b351c8247c58216a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2