1,10-Phenanthroline → HCID 131735187, compound

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Potassium bis(trimethylsilyl)amide	HCID 3251421	—
Reactant	(2-Bromoethynyl)tris(propan-2-yl)silane	HCID 11196280	—
Reactant	HCID 59746539	HCID 59746539	—
Reactant	HCID 131735185	HCID 131735185	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Diethyl Ether	HCID 3283	—
Product	HCID 131735187	HCID 131735187	76%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A suspension of t-butyl 4-morpholinobenzylcarbamate (1.11 g, 3.80 mmol), bromoethynyl-triisopropyl-silane, CuI (225 mg, 1.17 mmol) and 1,10-phenantroline (250 mg, 1.40 mmol) in dry toluene (7.5 ml) was warmed to 90° C. under a nitrogen atmosphere. KHMDS (10 ml, 0.5 M in toluene) was added dropwise under nitrogen atmosphere and the mixture was stirred for 12 hours at this temperature. The reaction mixture was cooled to RT; Et2O (30 ml) and NaCl/NH4OH (60/30 ml) were added and the organic phase was extracted with Et2O (3×30 ml), washed with NaCl/NH4 and dried over Na2SO4. The solvent was removed under reduced pressure to afford the title compound which was purified by column chromatography (PE/AcOEt:95/5).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09302998B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-1f5983b722ef418ebce8aaaf9318a9e9
Source note	uspto-grants-2016_04