Indole → HCID 21940715, compound

Participants

Role	Name	HCID	Charge
Reactant	Indole	HCID 798	—
Reactant	2-Chloropyridine	HCID 7977	—
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	HCID 21940715	HCID 21940715	410.5%

Reaction Steps

Using the general procedure, indole (0.117 g, 1.00 mmol) was coupled with 2-chloropyridine (113 μL, 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 (32 μL, 0.20 mmol, 20 mol %) and toluene (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 9:1) provided 0.194 g (100% yield) of the product as a yellow oil. 1H NMR (400 MHz, CDCl3): δ9.24 (s, 1H), 9.05 (s, 1H), 8.41 (s, 1H), 7.75 (m, 2H), 7.60 (m, 2H), 7.48 (m, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06759554B2
Source dataset	uspto-grants-2004_07
ORD ID	ord-9b7d3c6990f847d6841038515984a695
Source note	uspto-grants-2004_07