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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1875015Generated: October 30, 2026

Diisopropylethylamine → HCID 59451431, compound

https://huagongshe.com/reaction/1875015

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant4,6-dichloro-1H-indole-2-carbonyl chlorideHCID 2800756—
Reactant3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 59451392—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
ProductHCID 59451431HCID 5945143182.4%

Reaction Steps

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.16 mmol) in dichloromethane (1.5 mL) was added 4,6-dichloro-1H-indole-2-carbonyl chloride (0.060 g, 0.24 mmol) and diisopropylethylamine (0.031 g, 0.24 mmol). The resulting suspension was stirred at RT for 45 min. The reaction mixture was diluted with dichloromethane and water. A solid precipitated which was filtered and dried under vacuum to give the title compound (0.069 g, 82%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.12 (br. s., 1H), 9.20 (br. s., 1H), 7.77-7.78 (m, 1H), 7.41-7.52 (m, 3H), 7.33-7.41 (m, 2H), 7.23-7.32 (m, 1H), 7.19-7.20 (m, 1H), 4.54 (s, 2H). ES-LCMS: m/z 522 (M−H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08304419B2
Source datasetuspto-grants-2012_11
ORD IDord-f224d5f9c6d8439c88dfb3ee7aa25174
Source noteuspto-grants-2012_11