Dimethylformamide → 5-Methylthio-6-trifluoromethyl-1-{3-[2-(3-pyridyl)thiazol-4-yl]phenylcarbamoyl} indoline

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Bis-(1H-imidazol-2-YL)-methanone	HCID 5250894	—
Reactant	1H-Indole, 2,3-dihydro-5-(methylthio)-6-(trifluoromethyl)-	HCID 10657270	—
Reactant	[3-(2-Pyridin-3-yl-1,3-thiazol-4-yl)phenyl]amine	HCID 22724371	—
Solvent	Water	HCID 962	—
Solvent	Chloroform	HCID 6212	—
Solvent	Dichloromethane	HCID 6344	—
Product	5-Methylthio-6-trifluoromethyl-1-{3-[2-(3-pyridyl)thiazol-4-yl]phenylcarbamoyl} indoline	HCID 18005144	71.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A solution of 4-(3-aminophenyl)-2-(3-pyridyl)-thiazole (0.76 g, 3 mmol) in chloroform (30 ml) was added to a solution of carbonyl diimidazole (0.49 g, 3 mmol) in dichloromethane (10 ml). After 1 h the mixture was evaporated 5-Methylthio-6-trifluoromethyl indoline (0.7 g, 3 mmol) and N,N-dimethylformamide (20 ml) were added. The mixture was heated at 100° C. for 1 h, then diluted with water (50 ml). Filtraton and evaporated afforded a yellow solid (1.1 g). Recrystallisation from ethyl acetate-petrol afforded the title compound as a white solid (0.53 g, 35%), m.p. 154-5° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06638953B2
Source dataset	uspto-grants-2003_10
ORD ID	ord-af60f4c3e9044980a3c1242e95c8d9b3
Source note	uspto-grants-2003_10