Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-3-thienyl)-5-(2-furanyl)-1H-indole-7-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Furan-2-boronic acid	HCID 2734357	—
Reactant	5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide	HCID 59332563	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	3-(1,1-Dioxidotetrahydro-3-thienyl)-5-(2-furanyl)-1H-indole-7-carboxamide	HCID 59332559	36%

Reaction Conditions

Temperature	100 °C

Reaction Steps

5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide (0.050 g, 0.140 mmol) and 2-furanylboronic acid (0.020 g, 0.182 mmol) was dissolved in a 6:1 solution of 1,4 dioxane/water in a 20 mL microwave reaction vessel. Potassium carbonate (0.097, 0.70 mmol) was added and the solution was degassed with Argon. PdCl2(dppf) (0.017 g, 0.024 mmol) was added and the reaction was heated in a microwave at 100° C. for 10 min. The solution was passed through a StratoSphere SPE PL-Thiol MP SPE column to remove palladium and purified on Gilson preparative HPLC using Acetonitrile/0.1% NH4OH/H20. The desired fractions were concentrated, giving 0.017 g (36%) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08071584B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-57047065e2f246af90e4daedf0fab947
Source note	uspto-grants-2011_12