Potassium Phosphate, Tribasic → HCID 67288743, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Benzene, 1-bromo-4-(trifluoromethyl)-	HCID 67872	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	methyl 1H-indole-5-carboxylate	HCID 2737635	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 67288743	HCID 67288743	82.4%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of methyl indole-5-carboxylate 19a (2 g, 11.4 mmol), 1-bromo-4-trifluoromethyl-benzene 19b (2.8 g, 12.5 mmol), CuI (0.22 g, 1.14 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.54 mL, 3.43 mmol), and K3PO4 (6.06 g, 28.5 mmol) in toluene (12 mL) was heated at 110° C. for 7 h. The reaction mixture was diluted with CH2Cl2 and filtered. The solution was concentrated and the residue was purified by flash column chromatography (silica gel, 20% EtOAc/heptane) to give compound 19c (3.0 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748417B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-e5b21cec9cfa453992c41e2b5b1f3652
Source note	uspto-grants-2014_06