HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indoline → Adamantan-2-yl-(2,3-dihydro-indol-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indoline | HCID 10328 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Adamantanecarboxylic acid | HCID 303802 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Adamantan-2-yl-(2,3-dihydro-indol-1-yl)-methanone | HCID 71559641 | — |
Reaction Steps
A mixture of 24.2 mg (0.134 mmol) adamantane-2-carboxylic acid, 20 mg (0.168 mmol) indoline, 64.7 mg (0.2 mmol) TBTU and 43.4 mg (0.336 mmol) DIPEA in 1 mL DMF was stirred at room temperature overnight. Formic acid was added and the mixture was subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 14.1 mg (30%) of the title compound. MS(m/e): 282.4 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09090615B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-5084855ac78d47e5b4607fbee6b47503 |
| Source note | uspto-grants-2015_07 |