Sodium Carbonate → 4-Bromo-3',5'-dimethoxy-biphenyl-2,3-diamine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(3,5-Dimethoxyphenyl)boronic acid	HCID 4374257	—
Reactant	3,6-Dibromobenzene-1,2-diamine	HCID 11821532	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol	HCID 702	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-Bromo-3',5'-dimethoxy-biphenyl-2,3-diamine	HCID 59292878	37.9%

Reaction Conditions

Temperature	105 °C

Reaction Steps

A mixture of 3,5-dimethoxyphenylboronic acid (15.1 g, 82.7 mmol, 1.1 equiv) (Step 1.8) in EtOH (50 mL) was added dropwise to a mixture of 3,6-dibromo-benzene-1,2-diamine (20 g, 75.2 mmol) (Step 1.6), PdCl2(dppf) (6.1 g, 7.5 mmol, 0.1 equiv), Na2CO3 (2 M solution in H2O, 150 mL, 300.8 mmol, 4 equiv) in toluene (300 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 3 h, allowed to cool to rt, diluted with EtOAc and H2O and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (DCM) followed by trituration in EtOH to afford 9.2 g of the title compound as a white solid: ES-MS: 323.0/325.0 [M+H]+; tR=4.43 min (System 1); Rf=0.15 (DCM).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536175B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-99b0390f550b43afa7312b65ce2d7fbd
Source note	uspto-grants-2013_09