Diisopropylamine → N-(4-ethynyl-2-nitro-phenyl)-N,N',N'-trimethyl-propane-1,3-diamine

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Tetrafluoroboric acid	HCID 28118	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	HCID 16109013	HCID 16109013	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(benzonitrile)palladium chloride	HCID 498840	—
Solvent	Methanol	HCID 887	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(4-ethynyl-2-nitro-phenyl)-N,N',N'-trimethyl-propane-1,3-diamine	HCID 86602587	—

Reaction Steps

To N-(4-bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (940 mg, 2.97 mmol), Pd(PhCN)2Cl2 (34 mg, 0.09 mmol), CuI (11 mg, 0.06 mmol) and dioxane (4 mL) was added P(tBu)3.HBF4 (53 mg, 0.18 mmol), iPr2NH (0.50 mL, 3.6 mmol) and (trimethylsilyl)acetylene (0.49 mL, 3.6 mmol). The mixture was stirred for 3.5 h at RT, diluted with MeOH and stirred at RT with excess saturated aqueous K2CO3 for 2 h. The mixture was filtered through a pad of activated charcoal and concentrated to yield N-(4-ethynyl-2-nitro-phenyl)-N,N′, N′-trimethyl-propane-1,3-diamine. MS m/z=262 [M+1]+. Calc'd for C14H19N3O2: 261.33.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08476434B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-4a79f17e14d649e696f973ba160f5851
Source note	uspto-grants-2013_07