HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Methylcarbamoyl)benzeneboronic acid → 3-[2-(2-Methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-N-methyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(Methylcarbamoyl)benzeneboronic acid | HCID 2773524 | — |
| Reactant | (8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine | HCID 67481519 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | 3-[2-(2-Methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-N-methyl-benzamide | HCID 67481445 | — |
Reaction Steps
3-[2-(2-Methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-N-methyl-benzamide was prepared from (8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine (50.0 mg, 0.157 mmol) and 3-methylaminocarbonylbenzeneboronic acid (31.0 mg, 0.173 mmol) with Pd(dppf)Cl2 (0.012 g) as the catalyst in a manner analogous to Step 2c and was isolated as a yellow solid (0.048 g, 82%). MP=199-202° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.48-8.44 (m, 2H), 8.40 (dd, J=7.9, 1.3 Hz, 1H), 8.15 (d, J=7.8 Hz, 1H), 7.85 (d, J=7.8 Hz, 1H), 7.65-7.57 (m, 3H), 7.07-6.99 (m, 4H), 6.30 (br s, 1H), 3.92 (s, 3H), 3.07 (d, J=4.9 Hz, 3H). MS=374 (MH)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08501936B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-1fbe84f59e674bf6be183acb463c0dec |
| Source note | uspto-grants-2013_08 |