Dichloromethane → HCID 67405602, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(3-Phenylphenyl)boronic acid	HCID 2734315	—
Reactant	5-Chloro-2,3-dimethoxypyridine	HCID 22478560	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 67405602	HCID 67405602	34.2%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a mixture of 5-chloro-2,3-dimethoxypyridine (200 mg, 1.15 mmol), biphenyl-3-ylboronic acid (207 mg, 1.045 mmol), PdCl2(dppf).CH2Cl2 (43 mg, 0.052 mmol), under nitrogen, was added. THF (2.5 mL) followed by 1 M aqueous Na2CO3 solution (1.57 mL). The reaction mixture was heated at 150° C. (microwave irradiation) for 40 min, cooled to room temperature and partitioned between water and EtOAc. Layers were separated and the aqueous solution was extracted with EtOAc (2×). Combined organic solutions were dried over Na2SO4 and concentrated. Purification by flash chromatography (24 g silica gel, 1% to 20% EtOAc in hexanes) afforded 104 mg (34%) of 5-(biphenyl-3-yl)-2,3-dimethoxypyridine as a light yellow viscous liquid. LC/MS (M+H)+ 292.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09309199B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-e6e920864060480d99d8e48cf5a96b91
Source note	uspto-grants-2016_04