Benzophenone imine → HCID 86599737, compound

Participants

Role	Name	HCID	Charge
Reactant	Benzophenone imine	HCID 136809	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	(3R)-3-[6-(4-Bromo-phenyl)-pyridazin-3-yloxy]-1-aza-bicyclo[2.2.2]octane	HCID 67070015	—
Reactant	sodium 2-methylpropan-2-olate	HCID 178418730	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86599737	HCID 86599737	—

Reaction Steps

The product of Example 29D (360 mg, 1 mmol) was coupled with benzhydrylideneamine (Aldrich, 270 mg, 1.5 mmol) under the catalysis of Pd2(dba)3 (Aldrich, 18.3 mg, 0.02 mmol) and Xantphos (Strem Chemicals, 36 mg, 0.06 mmol) with t-BuONa (Aldrich, 150 mg, 1.5 mmol) in toluene (anhydrous, Aldrich, 10 mL) at 100° C. for 2 h. The mixture was then cooled down to ambient temperature and diluted with EtOAc (50 mL), washed with water (2×5 mL). The organic solution was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.4) as a solid (360 mg, yield, 78%). 1H NMR (300 MHz, CD3OD) δ 1.45-1.63 (m, 1H), 1.64-1.94 (m, 2H), 1.94-2.13 (m, 1H), 2.23-2.41 (m, 1H), 2.71-3.06 (m, 5H), 3.39-3.55 (m, 1H), 5.10-5.37 (m, 1H), 6.82-6.93 (m, 2H), 7.12-7.23 (m, 3H), 7.25-7.35 (m, 3H), 7.39-7.57 (m, 3H), 7.67-7.74 (m, 2H), 7.74-7.83 (m, 2H), 7.96 (d, J=9.2 Hz, 1H) ppm. MS (DCl/NH3): 461 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07309699B2
Source dataset	uspto-grants-2007_12
ORD ID	ord-3072058d4b1241b7bc7238a0eb4295ca
Source note	uspto-grants-2007_12