Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Fluorophenylboronic acid | HCID 2733986 | — |
| Reactant | Methyl 6-(bromomethyl)pyridine-2-carboxylate | HCID 21471714 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67974300 | HCID 67974300 | 19% |
Reaction Steps
A mixture of methyl 6-(bromomethyl)picolinate (0.264 g; 1.15 mmol), 3-fluorophenylboronic acid (0.190 g; 1.31 mmol), tetrakis(triphenylphosphine)palladium(0) (0.066 g; 0.057 mmol) and sodium carbonate (0.244 g; 2.30 mmol) in the mixture of water (1 mL) and 1,2-dimethoxyethane (3 mL) was heated at 130° C. in a microwave oven for 20 minutes. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent 0 to 6% of ethyl acetate in dichloromethane) to give 0.0524 g (19%) of methyl 6-(3-fluorobenzyl)picolinate as an oily residue.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266832B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-036ad602da284def821585293683eea7 |
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| Source note | uspto-grants-2016_02 |
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