Potassium Carbonate → 5-(3,5-Dimethyl-1H-pyrazol-4-yl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-bromo-3,5-dimethyl-1H-pyrazole	HCID 76937	—
Reactant	3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide	HCID 59332711	—
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	5-(3,5-Dimethyl-1H-pyrazol-4-yl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide	HCID 59332802	11%

Reaction Conditions

Temperature	120 °C

Reaction Steps

4-Bromo-3,5-dimethyl-1H-pyrazole (35 mg, 0.2 mmol), 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (30 mg, 0.072 mmol) and K2CO3 (50 mg, 0.36 mmol) was taken up in a 3:1 mixture of 1,4-dioxane/water (2 mL) in a microwave vial. The mixture was degassed by bubbling argon through it for 5 min. PdCl2(dppf) (8 mg, 0.011 mmol) was added, and the reaction was heated in a microwave for 10 min at 120° C. The reaction mixture was concentrated, diluted in DMSO, and purified on a Gilson HPLC(NH4OH buffer), giving 3 mg (11%) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08372875B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-2b5ab3d1e1174c0a85694469ecf2f654
Source note	uspto-grants-2013_02