Potassium Carbonate → N-(3-(4-Bromo-pyrazol-1-yl)-pyridin-2-yl)-2,2-dimethyl-propionamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromopyrazole	HCID 16375	—
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	N-(3-Iodopyridin-2-yl)-2,2-dimethylpropanamide	HCID 10946636	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Product	N-(3-(4-Bromo-pyrazol-1-yl)-pyridin-2-yl)-2,2-dimethyl-propionamide	HCID 59255076	53.4%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a mixture of N-(3-iodo-pyridin-2-yl)-2,2-dimethyl-propionamide (380 mg, 1.2 mmol) described in Manufacturing Example 39-1-2 and toluene (10 mL) were added 4-bromopyrazole (160 mg, 1.1 mmol), copper (I) iodide (11 mg, 0.056 mmol), trans-1,2-cyclohexanediamine (26 mg, 0.22 mmol) and potassium carbonate (340 mg, 2.5 mmol) at room temperature, which was stirred overnight at 110° C. The reaction mixture was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the title compound (190 mg, 52%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841327B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-46d5cd948674461d9956f6455fb5cacc
Source note	uspto-grants-2014_09