Sodium Carbonate → tert-Butyl 6-(1-methyl-1H-pyrazol-4-yl)-3-nitro-2-(quinolin-6-ylmethylamino)pyridin-4-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2773987	—
Reactant	Carbamic acid, N-[6-chloro-3-nitro-2-[(6-quinolinylmethyl)amino]-4-pyridinyl]-, 1,1-dimethylethyl ester	HCID 86672382	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-Butyl 6-(1-methyl-1H-pyrazol-4-yl)-3-nitro-2-(quinolin-6-ylmethylamino)pyridin-4-ylcarbamate	HCID 68315210	99.9%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a mixture of tert-butyl 6-chloro-3-nitro-2-(quinolin-6-ylmethylamino)pyridin-4-ylcarbamate (860 mg, 2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (416 mg, 2 mmol) and Na2CO3 (424 mg, 4 mmol) in dioxane (20 mL) and H2O (2 mL) under N2 was added Pd(dppf)Cl2 (163 mg, 0.2 mmol). The reaction was stirred at 80° C. under N2 overnight. After cooled to room temperature, the mixture was concentrated and purified by chromatography to afford the title compound (950 mg). MS (m/z): 476 (M+1)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987269B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-bbb3d8f9326a438da68595688f41dd51
Source note	uspto-grants-2015_03