Acetic Acid → HCID 58474352, compound

To a solution of 6-bromonicotinaldehyde (1.25 g, 6.72 mmol) in DCM (25 mL) was added 3-aminopropan-1-ol (1.514 g, 20.16 mmol) and acetic acid (0.385 mL, 6.72 mmol), and the reaction mixture was stirred for 10 min. Sodium triacetoxyborohydride (3.56 g, 16.80 mmol) was added and the reaction mixture was stirred at RT overnight. The reaction mixture was then diluted with EtOAc and extracted with water. The organic phase was discarded. The aqueous phase was concentrated and the resultant solid was stirred with a mixture of DCM and acetone then filtered. The filtrate was collected, dried over Na2SO4, and concentrated to give a yellowish material, which upon trituration with Et2O afforded title compound 196 (0.9 g, 55% yield) as an off-white solid. MS: 246 (MH+).

1. stirringthe reaction mixture was stirred at RT overnight
2. extractionextracted with water
3. concentrationThe aqueous phase was concentrated
4. stirringthe resultant solid was stirred with a mixture of DCM and acetone
5. filtrationthen filtered
6. customThe filtrate was collected
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customto give a yellowish material, which upon trituration with Et2O

ORD record

ord-508b80fd38b44b2a8a7fd6ac46f636f8

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906852B2