Sodium Carbonate → N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-6-methyl-2-pyridinecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	HCID 58268015	HCID 58268015	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-6-methyl-2-pyridinecarboxamide	HCID 44540227	—

Reaction Steps

A mixture of N-(6-bromo-1-methyl-1H-indazol-4-yl)-6-methyl-2-pyridinecarboxamide (50 mg, 0.14 mmol), indole-4-boranepinacoloate ester (40 mg, 0.18 mmol, commercially available), Pd(dppf)Cl2 (22 mg, 0.03 mmol) and sodium carbonate (2M aqueous, 0.26 ml) in 1,4-dioxane (2 ml) was heated to 150° C. under microwave conditions for 10 minutes. The mixture was extracted with dichloromethane (2×15 ml) and concentrated in vacuo and the residue was purified by HPLC (Method B) to afford the title compound (23 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765743B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-2acb486ef059418a9844bf49d0b37613
Source note	uspto-grants-2014_07