Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Acetamido-5-bromopyridine | HCID 293097 | — |
| Reactant | 3-tert-Butoxymethylphenylboronic acid | HCID 3773808 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 68631622 | HCID 68631622 | 72.1% |
Reaction Steps
Under an argon stream, 1.0 g of N-(5-bromopyridin-2-yl)acetamide, 967 mg of 3-(tert-butoxymethyl)phenylboronic acid and 269 mg of tetrakis(triphenylphosphine)-palladium are placed in a round-bottomed flask containing 30 ml of dimethoxyethane and 15 ml of a 2M solution of sodium carbonate degassed beforehand. The mixture is heated at 90° C. for 15 hours. After cooling, the reaction mixture is concentrated under reduced pressure. The residue is taken up between dichloromethane and water, the organic phase is separated and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue is then purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. The solid obtained is triturated with diethyl ether, recovered by filtration and then dried. 1.0 g of compound is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338451B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-587136aecea7428f8a44d1de29fdf82b |
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| Source note | uspto-grants-2012_12 |
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