Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | O-Xylene | HCID 7237 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-(Tributylstannyl)-1,3-benzothiazole | HCID 3762392 | — |
| Reactant | HCID 57934161 | HCID 57934161 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 136175573 | HCID 136175573 | 39.1% |
Reaction Steps
A mixture of acetic acid 3-{acetyl-[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-bromophenyl ester (50 mg) and dichlorobis(triphenylphosphine)palladium (II) (7 mg), xylene (1 ml) and 2-tributylstannylbenzothiazole (84 mg) was refluxed for 1.5 hours. The reaction mixture was cooled at room temperature, methanol (2 ml), water (1 ml) and potassium carbonate (50 mg) was added thereto, and the solution was vigourously stirred for 15 minutes at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate, then dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (20 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07612114B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-6b64a2e3cfd248729a096f8c7796ca6a |
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| Source note | uspto-grants-2009_11 |
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