Dichloromethane → HCID 66937071, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(5-Chloro-2-fluoropyridin-4-yl)boronic acid	HCID 44754822	—
Reactant	HCID 86650634	HCID 86650634	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Methanol	HCID 887	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 66937071	HCID 66937071	89.9%

Reaction Steps

A mixture of (R)-6-bromo-N-(6-oxaspiro[2.5]octan-1-yl)pyridin-2-amine (C, 100 mg, 0.35 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (136 mg, 0.77 mmol), PdCl2(dppf).CH2Cl2 adduct (23 mg, 0.028 mmol) in DME (1 mL) and 2M Na2CO3 (97 mg, 0.92 mmol) in a sealed tube was heated at 103° C. for 2 hr. The mixture was allowed to cool to ambient temperature and was diluted with EtOAc (˜25 mL) and MeOH (˜5 mL), filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 12 g, EtOAc/heptane=10/90 to 50/50]. Fractions were combined and concentrated in vacuo giving 105 mg of titled compound. LCMS (m/z): 334.0/336.0 [M+H]+, retention time=0.64 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08778951B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-f9b92c5907274224847df2a533da1836
Source note	uspto-grants-2014_07