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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1861325Generated: November 2, 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/1861325

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 (0.1 8 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 (0.1g, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06531599B2
Source datasetuspto-grants-2003_03
ORD IDord-af077090c45541eda44c95864b4785e9
Source noteuspto-grants-2003_03