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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 278646Generated: October 30, 2026

Dichloromethane → 4-[5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl]-2-fluoro-benzoic acid ethyl ester

https://huagongshe.com/reaction/278646

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantCyclopropylamineHCID 69828—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl esterHCID 12971712—
SolventAcetic AcidHCID 176—
SolventAcetonitrileHCID 6342—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
Product4-[5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl]-2-fluoro-benzoic acid ethyl esterHCID 12971713—

Reaction Steps

Following general procedure G and using 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)-benzoic acid ethyl ester (Compound 9, 0.132 g, 0.3 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL)and sodium cyanoborohydride (0.18 g, 2.86 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.1 g, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06359135B1
Source datasetuspto-grants-2002_03
ORD IDord-7405f2d12d8940a6a8414420298bc227
Source noteuspto-grants-2002_03