Hydrochloric Acid → HCID 58824205, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Oxygen	HCID 977	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Iodo-5-methoxypyridine	HCID 7010733	—
Reactant	5-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester	HCID 58824162	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 58824205	HCID 58824205	58.5%

Reaction Conditions

Temperature	95 °C

Reaction Steps

A mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (51) (126 mg), 2M aqueous cesium carbonate (0.6 mL) and 2-iodo-5-methoxypyridine (95 mg) in 1,4-dioxan (10 mL) under an argon atmosphere was sonicated to expel traces of oxygen. [1,1′-Bis-(diphenylphosphino) ferrocene]dichloropalladium (II) (8 mg) was added and the mixture heated at 95° C. for 18 hours. After cooling, the mixture was acidified to pH6 with 1M aqueous hydrochloric acid and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give compound 52 as an oil (70 mg), which was used directly in the next step. LC/MS System A: Rt=3.23 mins, m/z=354 ((M+H) for C20H19NO5).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07528157B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-6e3e81969e774875a9446bdb9ced16be
Source note	uspto-grants-2009_05