3-Heptanamine → 5-(3,4-Dichlorophenyl)-3-aminoheptane 4-amino-pyridine

Participants

Role	Name	HCID	Charge
Reactant	3-Heptanamine	HCID 34203	—
Reactant	3-Bromo-5-(3,4-dichlorophenyl)-4-amino-pyridine	HCID 22267317	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	Brain Injury Derived Neurotrophic Peptide (H-3914.0001)	HCID 102505550	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	5-(3,4-Dichlorophenyl)-3-aminoheptane 4-amino-pyridine	HCID 86585012	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo . The crude product is purified by flash chromatography to afford 3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06352990B1
Source dataset	uspto-grants-2002_03
ORD ID	ord-d212d5643d064c1aa8b036da5f204475
Source note	uspto-grants-2002_03