HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropyl chloroformate → Propan-2-yl (2-chloro-4-{3-cyano-1-cyclobutyl-6-[(pyrimidin-2-yl)oxy]-1H-indol-2-yl}phenyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropyl chloroformate | HCID 7917 | — |
| Reactant | 2-(4-amino-3-chloro-phenyl)-1-cyclobutyl-6-(pyrimidin-2-yloxy)-1H-indole-3-carbonitrile | HCID 59430670 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Propan-2-yl (2-chloro-4-{3-cyano-1-cyclobutyl-6-[(pyrimidin-2-yl)oxy]-1H-indol-2-yl}phenyl)carbamate | HCID 25050998 | 93% |
Reaction Steps
To 2-(4-amino-3-chloro-phenyl)-1-cyclobutyl-6-(pyrimidin-2-yloxy)-1H-indole-3-carbonitrile (0.26 g, 0.6 mmol) in CH2Cl2 (0.5 mL) and pyridine (0.5 mL) was added a solution of isopropyl chloroformate in toluene (1.0M, 0.8 mL) and the mixture was stirred at room temperature overnight. The mixture was diluted with aq. HCl (1N) and extracted with CH2Cl2. The organic layer was washed with water and brine, dried, concentrated and purified on silica gel (40% EtOAc/hexane) to provide {2-chloro-4-[3-cyano-1-cyclobutyl-6-(pyrimidin-2-yloxy)-1H-indol-2-yl]-phenyl}-carbamic acid isopropyl ester (0.29 g, 93%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07973069B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-4de65736a21b45b1ae1036c5aaf2ec48 |
| Source note | uspto-grants-2011_07 |