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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 77814Generated: October 29, 2026

Trifluoroacetic acid → 4-(5-(2-Amino-pyridin-3-yl)isoxazol-3-ylmethyl)phenol

https://huagongshe.com/reaction/77814

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantThioanisoleHCID 7520—
ReactantSodium BicarbonateHCID 516892—
Reactant3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamineHCID 16061508—
SolventEthyl AcetateHCID 8857—
Product4-(5-(2-Amino-pyridin-3-yl)isoxazol-3-ylmethyl)phenolHCID 25114386100%

Reaction Steps

To a mixture of 3-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (32 mg, 0.090 mmol) described in Example 1 and trifluoroacetic acid (1 mL) was added thioanisole (45 mg, 0.36 mmol) at room temperature, which was stirred for 2 hours at the same temperature. To a mixture of saturated aqueous sodium hydrogencarbonate solution and ethyl acetate was added the reaction mixture. The organic layer was separated and washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=4:1) to obtain the title compound (24 mg, 100%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841327B2
Source datasetuspto-grants-2014_09
ORD IDord-bf46d41806ab4fddae53589c10e3d18e
Source noteuspto-grants-2014_09