HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-N-[(3-hydroxyphenyl)methyl]-2,3-dihydro-(2S)-1H-indole-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Aminomethyl)phenol hydrochloride | HCID 22058427 | — |
| Reactant | 1-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-2,3-dihydro-(2S)-1H-indole-2-carbonyl chloride | HCID 86612301 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-N-[(3-hydroxyphenyl)methyl]-2,3-dihydro-(2S)-1H-indole-2-carboxamide | HCID 66846804 | 51% |
Reaction Steps
54 mg (0.53 mmol) of triethylamine are added to a suspension of 42.26 mg (0.265 mmol) of 3-(aminomethyl)phenol hydrochloride in 8 ml of dichloromethane at ambient temperature, then a solution of 100 mg (0.265 mmol) of 1-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-2,3-dihydro-(2S)-1H-indole-2-carbonyl chloride in 2 ml of dichloromethane is added over 10 minutes. This is left to agitate at ambient temperature for 1 hour. The reaction medium is washed with water, dried on magnesium sulfate, the solvents are evaporated and the evaporation residue is purified by silica column chromatography eluting with the help of a toluene/ethyl acetate mixture (8/2; v/v). The expected product is obtained in the form of a white solid with a yield of 51%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07872021B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-3ce820595df44cd1a864c66f3ae51e86 |
| Source note | uspto-grants-2011_01 |