Morpholine → tert-butyl 6'-morpholino-2,3,5,6-tetrahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]-1'(2'H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Morpholine	HCID 8083	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	tert-butyl 6'-bromo-2,3,5,6-tetrahydrospiro-[pyran-4,3'-pyrrolo[3,2-b]pyridine]-1'(2'H)-carboxylate	HCID 67284572	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	tert-butyl 6'-morpholino-2,3,5,6-tetrahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]-1'(2'H)-carboxylate	HCID 67284807	—

Reaction Steps

Prepared according to procedure N using tert-butyl 6′-bromo-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]-1′(2′H)-carboxylate (12.0 g, 32.5 mmol), morpholine (3.11 mL, 35.7 mmol), Pd2dba3 (1.19 g, 1.30 mmol), XPhos (1.24 g, 0.08 mmol) and sodium tert-butoxide (6.25 g, 65.0 mmol) in toluene (200 mL) at 110° C. for 5 h. Purification by column chromatography (hexanes:EtOAC, 1:0 to 1:3 as eluent) gave tert-butyl 6′-morpholino-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]-1′(2′H)-carboxylate. Mass Spectrum (ESI) m/e=376.2 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765940B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-6a6148cf4e804bc6a959f2c18766de44
Source note	uspto-grants-2014_07