Indole → 1-(2-Aminophenyl)indole

Participants

Role	Name	HCID	Charge
Reactant	Indole	HCID 798	—
Reactant	2-Bromoaniline	HCID 11992	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl acetate hexane	HCID 21226206	—
Product	1-(2-Aminophenyl)indole	HCID 11513988	71.1%

Reaction Steps

Using the general procedure, indole (0.117 g, 1.00 mmol) was coupled with 2-bromoaniline (0.206 g, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %) and toluene (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 5:1) provided 0.148 g (71% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.64 (m, 1H), 7.18 (m, 6H), 6.82 (m, 2H), 6.64 (m, 1H), 3.52 (bs, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115784B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-2cdb2cf863ec4e4395cb02aab7f59443
Source note	uspto-grants-2006_10