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

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Bromopyridine-2-carboxylic Acid	HCID 2050129	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	5,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine	HCID 13247046	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-bromo-6-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}pyridine	HCID 59525609	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08367706B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-ef6d136ec9034e4880c918885b1dd270
Source note	uspto-grants-2013_02