N,N'-Dimethylethylenediamine → 5-(1-phenyl-1H-1,2,3-triazol-4-yl)indolin-2-one

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Iodobenzene	HCID 11575	—
Reactant	Sodium Azide	HCID 33557	—
Reactant	Sodium Ascorbate	HCID 23667548	—
Reactant	HCID 90418779	HCID 90418779	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethanol	HCID 702	—
Solvent	Water	HCID 962	—
Product	5-(1-phenyl-1H-1,2,3-triazol-4-yl)indolin-2-one	HCID 90417890	76.7%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a mixture of iodobenzene (204 mg, 1 mmol), sodium azide (130 mg, 2 mmol), sodium carbonate (53 mg, 0.5 mmol), CuI (19 mg, 0.1 mmol), sodium ascorbate (20 mg) and N,N′-dimethylethylenediamine (18 ul, 0.2 mmol) in EtOH (1.5 ml) and water (0.5 ml) were added 5-((trimethylsilyl)ethynyl)indolin-2-one (115 mg, 0.5 mmol), and stirred at 80° C. for 2 h. After cooling to ambient temp, EtOH was removed under reduced pressure. The residue was suspended in EtOH and stirred for 1 h at rt and filtered. The filtrate was washed with water and hexane and dried under vacuo to give 5-(1-phenyl-1H-1,2,3-triazol-4-yl)indolin-2-one (106 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09227962B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-082e19c0c39b4f7b9eed21deada74a06
Source note	uspto-grants-2016_01