Triethylamine → 1-({5-[2-Chloro-5-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Chloro-5-(methylsulphonyl)benzoic acid	HCID 2329132	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 178438386	HCID 178438386	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-({5-[2-Chloro-5-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile	HCID 57800218	26.1%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A solution was prepared using 2-[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol), 2-chloro-5-(methylsulfonyl)benzoic acid (0.108 g, 0.463 mmol), HATU (0.176 g, 0.463 mmol), triethylamine (0.047 g, 0.463 mmol) and anhydrous DMF (10 mL). The mixture was then heated in a microwave at 150° C. for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.042 g (26% yield) of pure product: MS (ES) m/z 522 (M+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07572820B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-23cb2ea62d174f3595aec1c338002554
Source note	uspto-grants-2009_08