HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Chloro-4-fluoroaniline → 2-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Chloro-4-fluoroaniline | HCID 9708 | — |
| Reactant | 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester | HCID 86703101 | — |
| Reactant | 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester | HCID 86703105 | — |
| Reactant | 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one | HCID 86703124 | — |
| Product | 2-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one | HCID 86703123 | — |
Reaction Steps
The title compound was prepared in analogy to the procedure described for Step D2, but 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step E4) and 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one (Step O4) were used instead of 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 3-chloro-4-fluoroaniline respectively to afford the title compound as a green-blue foam. tR: 5.47 min (HPLC 1); ESI-MS: tR=1.33 min, [M+H]+ 568/570/572 (LC-MS 1); TLC: Rf=0.30 (1:1 EtOAc/heptanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365576B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-c99e317e2cba4a9091afce2f133fd4c2 |
| Source note | uspto-grants-2016_06 |