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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1376153Generated: October 31, 2026

Triethylamine → 5-Chloro-N-(6-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-indole-2-carboxamide

https://huagongshe.com/reaction/1376153

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant5-Chloro-1H-indole-2-carboxylic acidHCID 82693—
Reactant3-amino-6-fluoro-3,4-dihydro-2(1H)-quinolinone monohydrochlorideHCID 12761411—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product5-Chloro-N-(6-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-indole-2-carboxamideHCID 1021555785%

Reaction Steps

Triethylamine (184 μL, 1.32 mmol), HOBt (89 mg, 0.66 mmol), 3-amino-6-fluoro-3,4-dihydro-2(1H)-quinolinone monohydrochloride (CAS Reg. No: 82420-54-0) (143 mg, 0.66 mmol), and EDAC (127 mg, 0.66 mmol) were added to a solution of 5-chloroindole-2-carboxylic acid (129 mg, 0.66 mmol) in anhydrous DMF (3.5 mL). The reaction was stirred at ambient temperature for approximately 16 h, and then poured into water (50 mL). This was stirred vigorously for about 10 mins. and filtered. The collected precipitate was washed with water and dried in vacuum at 40° C., to give the title compound (200 mg, 85%) as an amorphous solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07169927B2
Source datasetuspto-grants-2007_01
ORD IDord-132b1a1a7b7b4544854944b431453297
Source noteuspto-grants-2007_01