HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-(5-(2-Amino-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)-pyridin-2-ylamine | HCID 16061508 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(5-(2-Amino-pyridin-3-yl)isoxazol-3-ylmethyl)phenol | HCID 25114386 | 100% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07691882B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-4779ba607dbf40fd92f798cae36f8ea8 |
| Source note | uspto-grants-2010_04 |