4-Bromo-2-nitroaniline → 4-(3-Dimethylamino-prop-1-ynyl)-2-nitro-phenylamine

Participants

Role	Name	HCID	Charge
Reactant	4-Bromo-2-nitroaniline	HCID 70132	—
Reactant	N,N-Dimethylpropargylamine	HCID 81643	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Product	4-(3-Dimethylamino-prop-1-ynyl)-2-nitro-phenylamine	HCID 118024614	100.3%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a stirred solution of 4-bromo-2-nitro-phenylamine (1.08 g, 5 mmol) and dimethyl-prop-2-ynyl-amine (1.0 g, 12 mmol) in TEA (20 mL) was added Pd(PPh3)2Cl2 (0.7 g, 1 mmol) and CuI (360 g, 2 mmol). The solution was stirred at 60° C. under nitrogen for 3 hours. The solution was evaporated with silica gel and purified by flash chromatography on silica to give the title compound (1.1 g, 70% purity). The title compound was taken directly to the next step without further purification. MS (ESI) 221 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434697B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-7785647e4fe445b2be9d75300737977f
Source note	uspto-grants-2016_09