4-Methoxybenzylamine → 1-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine

Participants

Role	Name	HCID	Charge
Reactant	4-Methoxybenzylamine	HCID 75452	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	6-bromo-1-isopropyl-1H-imidazo[4,5-c]pyridine	HCID 90177760	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene	HCID 1140	—
Product	1-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine	HCID 118036800	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 6-bromo-1-isopropyl-1H-imidazo[4,5-c]pyridine (intermediate 256, 2.134 g, 8.80 mmol), 4-methoxybenzylamine (1.389 ml, 10.38 mmol), NaOt-Bu (1.308 g, 13.20 mmol), Pd(OAc)2 (0.14 g, 0.616 mmol) and Xantphos (0.367 g, 0.616 mmol) in toluene (90 ml) was evacuated and purged with argon (3×) and then heated to 100° C. After 17 h, the reaction mixture was quenched with H2O and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266883B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-21124ef1873e45b0addb797ea6fc6009
Source note	uspto-grants-2016_02