Acetic Acid → HCID 59620027, compound

A solution of 3-amino-5-bromopyridine (Aldrich, Buchs, Switzerland, 400 mg, 2.31 mmol), acetic acid (0.4 ml, 6.99 mmol) and acetaldehyde (Fluka, Buchs, Switzerland, 153 mg, 3.47 mmol) in dichloromethane was stirred for 1.5 h at rt then was added sodium triacetoxyborohydride (980 mg, 4.62 mmol). The reaction mixture was stirred 17.5 h at rt then were added at 1.5 h interval acetaldehyde (153 mg, 3.47 mmol) and sodium tracetoxyborohydride (490 mg, 2.31 mmol). The RM was stirred 7 h at rt then were added at 1.5 h interval acetaldehyde (77 mg, 1.75 mmol) and sodium tracetoxyborohydride (490 mg, 2.31 mmol). After 15 h stirring at rt, the reaction mixture was diluted with dichloromethane and quenched with saturated aqueous NaHCO3. The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography (DCM/iPrOH 1% to 3.5%) to give the title compound as a yellowish oil. (HPLC: tR 2.31 min (Method A); M+H=229, 231 MS-ES)

1. stirringThe RM was stirred 7 h at rt
2. stirringAfter 15 h stirring at rt
3. customquenched with saturated aqueous NaHCO3
4. extractionThe aqueous layer was extracted with dichloromethane
5. dry with materialthe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. customThe crude product was purified by flash chromatography (DCM/iPrOH 1% to 3.5%)

ORD record

ord-fc8cef85b86044eca25294586a74c68a

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2