1-tert-butyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → tert-butyl 4-(6-(6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	1-tert-butyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 53217109	—
Reactant	tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate	HCID 86707047	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Sodium Carbonate	HCID 10340	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-butyl 4-(6-(6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate	HCID 86707048	53%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 1-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (220 mg, 0.88 mmol), tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (377 mg, 0.88 mmol), and Pd(dppf)Cl2 (64 mg, 0.088 mmol) in 1,4-dioxane (20 mL) and Na2CO3 (2.0 M, 5 mL) under nitrogen was heated at 100° C. for 20 hours. The crude product was purified by silica gel chromatography using petroleum ether:EtOAc (50%-100%) as eluting solvents to afford tert-butyl 4-(6-(6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a yellow solid (240 mg, 53%). MS (ESI) m/z: 517 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434725B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-274c87d39a6e4be2b78c1c38aa1afcec
Source note	uspto-grants-2016_09