Sodium Carbonate → HCID 86676682, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2774010	—
Reactant	5-Bromo-1H-pyrazolo[3,4-c]pyridine	HCID 45789778	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethoxyethane ethanol	HCID 20074477	—
Product	HCID 86676682	HCID 86676682	43.2%

Reaction Steps

To a solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine (100 mg, 0.5 mmol) in DME:EtOH (5:1, 5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (116 mg, 0.6 mmol). Under argon, the mixture was stirred under microwave irradiation for 60 min at 150. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine (40 mg, 43%). 1H NMR (500 MHz, MeOD) δ 9.17 (s, 1H), 8.98 (s, 1H), 8.17 (m, 3H), 8.05 (d, J=1.5, 1H). ESI MS m/z=186.1 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09260425B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-319b0a66eaf34230a59f91521b0792d6
Source note	uspto-grants-2016_02