Pyrazole → 2-Methoxy-4-(1H-pyrazol-1-yl)aniline

Participants

Role	Name	HCID	Charge
Reactant	Pyrazole	HCID 1048	—
Reactant	Sodium Chloride	HCID 5234	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromo-2-methoxyaniline	HCID 459257	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	2-Methoxy-4-(1H-pyrazol-1-yl)aniline	HCID 59794359	90%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a solution of 4-bromo-2-(methyloxy)aniline (400 mg, 1.979 mmol) in anh. NMP (4 mL), at r.t., under N2, were added pyrazole (269 mg, 2 eq), K2CO3 (819 mg, 3 eq), CuI (377 mg, 1 eq) and (1R,2R)-diaminomethylcyclohexane (281 mg, 1 eq). The reaction mixture was stirred at 150° C. for 3 hr. It was cooled down to r.t. and poured into EtOAc/sat.aq. NaCl. The phases were separated and the organic layer was washed with sat.aq. NH4Cl (20 mL) and sat.aq. NaCl (20 mL). The combined aqueous layers were extracted back with EtOAc (20 mL) and the combined organic extracts were dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7:3) to give the title compound as a brown oil (336 mg, 90%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07427630B2
Source dataset	uspto-grants-2008_09
ORD ID	ord-9dae480e5d5e4f97b07f3895141283dc
Source note	uspto-grants-2008_09