HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methyl-2-(tributylstannyl)pyridine → Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methyl-2-(tributylstannyl)pyridine | HCID 16427098 | — |
| Reactant | Methyl 3-bromo-6-methylpyridine-2-carboxylate | HCID 90404668 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate | HCID 90412135 | 18.9% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
To the title compound of step B (509 mg, 2.2 mmol) and the title compound of step C (1.1 g, 2.9 mmol) in PhCH3 (6.6 mL) was added Pd(PPh3)4 (225 mg, 0.2 mmol). The reaction was degassed with N2 and heated at 150° C. for 1.5 h using microwave reactor. The reaction was cooled to rt, diluted with H2O and extracted with EtOAc. The organic layer was dried (MgSO4). Purification via silica gel chromatography (0-100% EtOAc in heptane) gave the title compound (101 mg, 18%). MS (ESI) mass calcd. for C14H14N2O2, 242.3; m/z found 243 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09062078B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-8354ce1514984632a8d94ed947c04494 |
| Source note | uspto-grants-2015_06 |