1,10-Phenanthroline → (4-Morpholin-4-yl-phenyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid tert-butyl ester

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	tert-Butyl [4-(morpholin-4-yl)phenyl]carbamate	HCID 11482840	—
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	(4-Morpholin-4-yl-phenyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid tert-butyl ester	HCID 131735184	40%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A suspension of t-butyl 4-morpholinophenylcarbamate (1.45 g, 7.60 mmol), bromoethynyl-triisopropyl-silane, CuI (450 mg, 2.34 mmol) and 1,10-phenantroline (500 mg, 2.80 mmol) in dry toluene (15 ml) was warmed up to 90° C. under a nitrogen atmosphere. KHMDS (20 ml, 0.5 M in toluene) was added dropwise under nitrogen and the mixture was stirred for 12 hours at this temperature. The reaction was cooled down 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 and the title compound was obtained after purification 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-d61fd1e97bff4e30ba7fa4966a0c6859
Source note	uspto-grants-2016_04