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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1H-Indole-4-boronic acid	HCID 2763173	—
Reactant	N-(6-Bromo-1H-indazol-4-yl)-2-pyridinecarboxamide	HCID 58255852	—
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	N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide	HCID 44540407	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of N-(6-bromo-1H-indazol-4-yl)-2-pyridinecarboxamide (38 mg, 0.12 mmol), 1H-indol-4-ylboronic acid (23 mg, 0.14 mmol, available from Apollo), Pd(dppf)Cl2 (10 mol %, 12 mg, 0.015 mmol), aqueous sodium carbonate solution (2M, 0.18 ml, 0.36 mmol) in dioxane/water 1:1 (2 ml) was heated at 150° C. for 30 mins under microwave irradiation. The reaction mixture was filtered through a silica cartridge eluting with MeOH, then the solvent was removed in vacuo. Purification by mass directed preparative HPLC (Method B) give after evaporation of solvents the title compound as a light brown solid (21 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765743B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-9f550ca3a76d4cadb710f4f9dff69423
Source note	uspto-grants-2014_07