HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-(5-(2-Amino-5-fluoro-pyridin-3-yl)-isoxazol-3-ylmethyl)-phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Thioanisole | HCID 7520 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-5-fluoro-pyridin-2-ylamine | HCID 59255454 | — |
| Product | 4-(5-(2-Amino-5-fluoro-pyridin-3-yl)-isoxazol-3-ylmethyl)-phenol | HCID 59255520 | 98% |
Reaction Steps
To a trifluoroacetic acid (5 mL) solution of 3-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-5-fluoro-pyridin-2-ylamine (180 mg, 0.48 mmol) described in Example 173 was added thioanisole (225 μL, 1.92 mmol), which was stirred for 6 hours at room temperature. A saturated sodium hydrogencarbonate aqueous solution was added to this reaction solution at 0° C., which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:2˜ethyl acetate) to obtain the title compound (134.0 mg, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07691882B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-7ddc9bb70fe347daa52a53bf0b447816 |
| Source note | uspto-grants-2010_04 |