Thiomorpholine → 4-(5-Bromopyridin-2-yl)thiomorpholine

Participants

Role	Name	HCID	Charge
Reactant	Thiomorpholine	HCID 67164	—
Reactant	5-Bromo-2-iodopyridine	HCID 593690	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	sodium 2-methylpropan-2-olate	HCID 178418730	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	4-(5-Bromopyridin-2-yl)thiomorpholine	HCID 17749962	—

Reaction Conditions

Temperature	98 °C

Reaction Steps

A mixture of thiomorpholine (1.03 g, 10.0 mmol), 5-bromo-2-iodopyridine (3.69 g, 13 mmol), Pd2(dba)3 (200 mg, 0.2 mmol), xantphos (510 mg, 0.6 mmol) and t-BuONa (1.44 g, 15 mmol) in toluene (50 ml) was stirred under argon at 98° C. for 3 hours. After cooled to room temperature, the mixture was filtered through celite and washed with ethyl acetate. The filtrate was evaporated and the residue was subjected to silica gel column chromatography with 0-5% ethyl acetate in hexanes as eluent to give 4-(5-bromopyridin-2-yl)thiomorpholine 219-2 as solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238646B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-298737c17fd94fb5831160e996eede4a
Source note	uspto-grants-2016_01