HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromo-3,5,6-trifluoropyridine → (R)-ethyl 3-((6-bromo-3,5-difluoropyridin-2-yl)amino)-4,4-dimethylpentanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromo-3,5,6-trifluoropyridine | HCID 45790725 | — |
| Reactant | 2-Chloro-5,6-difluoronicotinonitrile | HCID 73554808 | — |
| Reactant | (R)-ethyl 3-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)-3-(1-methylcyclopentyl)propanoate | HCID 86714767 | — |
| Reactant | (R)-ethyl 3-((6-bromo-3,5-difluoropyridin-2-yl)amino)-4,4-dimethylpentanoate | HCID 86714771 | — |
| Reactant | HCID 178427251 | HCID 178427251 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (R)-ethyl 3-((6-bromo-3,5-difluoropyridin-2-yl)amino)-4,4-dimethylpentanoate | HCID 86714771 | — |
| Product | HCID 178445894 | HCID 178445894 | — |
Reaction Steps
Compound 6 was synthesized in a manner similar to compound 12, utilizing (R)-ethyl 3-((6-bromo-3,5-difluoropyridin-2-yl)amino)-4,4-dimethylpentanoate as the intermediate for the Suzuki coupling. (R)-ethyl 3-((6-bromo-3,5-difluoropyridin-2-yl)amino)-4,4-dimethyl-pentanoate was prepared in the same fashion as intermediate, 143a, utilizing 2-bromo-3,5,6-trifluoropyridine as the starting material instead of 2-chloro-5,6-difluoropyridine-3-carbonitrile: 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=6.4 Hz, 1H), 8.06 (s, 1H), 7.06 (t, J=9.7 Hz, 1H), 4.58 (s, 2H), 2.80 (d, J=13.2 Hz, 1H), 2.29 (dd, J=13.3, 8.7 Hz, 1H), 0.98 (s, 9H).; LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.92 min, (M+H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09051319B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-1dc73053d0914091ae996f86f7a8d982 |
| Source note | uspto-grants-2015_06 |