Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Methyl 5-bromo-6-chloronicotinate | HCID 2764313 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21109713 | HCID 21109713 | 50% |
Reaction Steps
A mixture of 0.3 g (1.27 mmol) 5-bromo-6-chloro-nicotinic acid methylester and 0.34 g (3.17 mmol) benzylamine in 0.4 mL DMSO was heated to 160° C. in the microwave for 4 min. 0.6 mL water and 0.4 mL 5N KOH aq was added and heated to 160° C. in the microwave for 2 min. Acetic acid and DMF was added and the mixture was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/HCOOH. The combined product fractions were evaporated to yield 0.195 g (50%) of the title compound. MS (m/e): 307.1 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07229999B2 |
|---|
| Source dataset | uspto-grants-2007_06 |
|---|
| ORD ID | ord-2c87b990f74c485ab5f4ebd9bb9a00e2 |
|---|
| Source note | uspto-grants-2007_06 |
|---|