Water → Tert-butyl 4-[4-(5-amino-3-methylisoxazol-4-yl)phenyl]piperazine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-(4-BOC-Piperazino)phenylboronic acid	HCID 5233014	—
Reactant	4-Bromo-3-methylisoxazol-5-amine	HCID 10487519	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Tert-butyl 4-[4-(5-amino-3-methylisoxazol-4-yl)phenyl]piperazine-1-carboxylate	HCID 22236112	—

Reaction Conditions

Temperature	95 °C

Reaction Steps

To 4-bromo-3-methylisoxazol-5-amine (2.63 g, 14.85 mmol), 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (5.7 g, 18.57 mmol, prepared as described in Example 1) and catalyst PdCl2(dppf) (365 mg, 0.45 mmol) in DMF (100 mL) under dry nitrogen was added aqueous sodium carbonate (2.0 M, 18.6 mL, 37 mmol). The reaction was heated to 95° C. for 1 hour and an additional aliquot of PdCl2(dppf) (365 mg, 0.45 mmol) was added and the reaction mixture was heated overnight. Water was added and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6, then 1/1) to afford tert-butyl 4-[4-(5-amino-3-methylisoxazol-4-yl)phenyl]piperazine-1-carboxylate.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07012075B2
Source dataset	uspto-grants-2006_03
ORD ID	ord-c1605f9545074d56836b9af62f469499
Source note	uspto-grants-2006_03