Dimethylformamide → 2-bromo-6-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}pyridine

A solution of HOBt (148 mg, 0.97 mmol), DIEA (130 μL, 0.74 mmol), HATU (367 mg, 0.97 mmol), bromopyridine-2-carboxylic acid (150 mg, 0.74 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (91 mg, 0.74 mmol) in DMF (2.5 mL) was stirred overnight at 65° C. Upon completion, Si-carbonate (2.8 g, 2.23 mmol) and DCM (3 mL) were added and the mixture was shaken overnight at room temperature. The resulting mixture was then filtered, washed with DCM, concentrated in vacuo and purified by reverse phase HPLC (acetonitrile/water+formic acid modifier) to afford the title compound.

1. filtrationThe resulting mixture was then filtered
2. washwashed with DCM
3. concentrationconcentrated in vacuo
4. custompurified by reverse phase HPLC (acetonitrile/water+formic acid modifier)

ORD record

ord-ef6d136ec9034e4880c918885b1dd270

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2