Methyl 3-mercaptopropionate → Methyl 3-(2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Methyl 3-mercaptopropionate	HCID 18050	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N-(3-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine	HCID 86631504	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 3-(2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate	HCID 86631505	87.2%

Reaction Conditions

Temperature	95 °C

Reaction Steps

A mixture of N-(3-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine (0.55 g, 1.79 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.052 g, 0.090 mmol), Pd2dba3 (0.041 g, 0.045 mmol), methyl 3-mercaptopropanoate (0.21 mL, 1.88 mmol), N-ethyl-N-isopropylpropan-2-amine (0.62 mL, 3.60 mmol), and dioxane (40 mL) was heated to 95° C. under nitrogen. Cooled to ambient temperature and filtered the solids. Concentrated and purified by MPLC (Biotage) eluting with 1:1 hexane:ethyl acetate to afford the title compound (0.541 g, 87% yield) as a dark yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883828B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-4552770fe4b74bea91f4f80720d01eba
Source note	uspto-grants-2014_11