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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1854832Generated: October 31, 2026

3-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → methyl 8-(4-amino-2-fluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

https://huagongshe.com/reaction/1854832

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 44755207—
ReactantMethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylateHCID 86696543—
Productmethyl 8-(4-amino-2-fluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylateHCID 8669655069.8%

Reaction Steps

Methyl 8-(4-amino-2-fluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline (122 mg, 0.51 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 94:6) afforded the title compound as a yellow solid (87 mg, 64%). ESI-MS m/z: 367 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08962842B2
Source datasetuspto-grants-2015_02
ORD IDord-12cc1cf3355f4780ab5ff37c5802253a
Source noteuspto-grants-2015_02