HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 69311233, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1H-Indazol-5-amine | HCID 88012 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 69311233 | HCID 69311233 | 95% |
Reaction Steps
Into a solution of 5-aminoazaindole (0.6 g, 4.5 mmol) in dry DMF (11 mL) N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (TBTU, 1.45 g, 9 mmol), 1-hydroxybenzotriazole (HOBt, 0.69 g, 9 mmol) and glacial AcOH (260 micro), diisopropylethylamine (DIPEA, 3.12 mL, 18 mmol) was slowly dropped in ca. 30′ under stirring. The reaction mixture was stirred at room temperature for 18 h, concentrated and the residue was purified by flash chromatography eluting with dichloromethane/MeOH 10:1. The desired 1H-pyrrolo[2,3-b]pyridin-5-ylacetamide (title compound) was obtained in 95% yield (0.78 g, 4.2 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07371862B2 |
| Source dataset | uspto-grants-2008_05 |
| ORD ID | ord-96ec231f5a0d46fbb706c2b18e5e006e |
| Source note | uspto-grants-2008_05 |