Triethylamine → HCID 64124842, compound

Glycine ethyl ester hydrochloride (9C2) (161 mmol, 22.51 g) was dried under vacuum then dissolved in methanol (200 ml). Triethylamine (137 mmol, 13.87 g) was added with stirring and the resulting solution was added dropwise to a solution of 5-bromo-2-formylpyridine (9B1) (81 mmol, 15 g) in methanol (200 ml) under nitrogen. After 30 min, sodium triacetoxyborohydride (194 mmol, 41.0 g) was added portionwise over 30 min and the reaction was then stirred at room temperature under nitrogen overnight. The reaction was quenched with saturated sodium bicarbonate solution and extracted three times with DCM. The combined organic layers were washed with water, brine and dried using a hydrophobic frit, then concentrated under reduced pressure. The reside was purified on silica eluting with heptane/EtOAc/EtOH 8/1.6/0.4 to 5/4/1 to give ethyl 2-((5-bromopyridin-2-yl)methylamino)acetate (9J1) 11.4 g (51.6%); 1H NMR (400 MHz, CDCl3) 8.61 (s, 1H) 7.78 (d, 1H) 7.27 (d, 1H) 4.20 (q, 2H) 3.91 (s, 2H) 3.46 (s, 2H) 2.31 (bs, 1H) 1.27 (t, 3H).

1. stirringthe reaction was then stirred at room temperature under nitrogen overnight
2. customThe reaction was quenched with saturated sodium bicarbonate solution
3. extractionextracted three times with DCM
4. washThe combined organic layers were washed with water, brine
5. customdried
6. concentrationconcentrated under reduced pressure
7. customThe reside was purified on silica eluting with heptane/EtOAc/EtOH 8/1.6/0.4 to 5/4/1

ORD record

ord-711eea29b7c146019ed58da8a6770084

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507521B2