Diisopropylamine → HCID 5247662, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	5,5'-DIBROMO-2,2'-BIPYRIDINE	HCID 10903103	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 5247662	HCID 5247662	—

Reaction Steps

Firstly, a mixture of 5,5′-dibromo-2,2′-bipyridyl (300 mg, 0.96 mmol), PdCl2(PPh3)2 (60 mg, 0.085 mmol) and CuI (30 mg, 0.16 mmol) was added with dist. THF (18 mL), dist. i-Pr2NH (2.4 mL) and trimethylsilylacetylene (467 μL, 3.3 mmol). The resultant mixture was then stirred under a nitrogen atmosphere at room temperature for 29 hours to obtain a reaction mixture. Subsequently, a salt contained in the reaction mixture was removed through a celite filtration process. The organic layer thus obtained was concentrated to obtain a crude product (I) Then, the obtained crude product (I) was separated and purified by silica gel column chromatography (CH2Cl2=100) to obtain 5,5′-bis(trimethylsilylethynyl)-2,2′-bipyridyl.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08053588B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-74b63bfd3d7045f9a49e092faedae426
Source note	uspto-grants-2011_11