HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → N-Benzyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid | HCID 21907018 | — |
| Solvent | Water | HCID 962 | — |
| Product | N-Benzyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide | HCID 57595724 | 27.6% |
Reaction Steps
Into a Round bottom flask was added compound 15 (35.0 mg, 0.000216 mol) and benzylamine (0.05 mL, 0.0004 mol) and PyBroP (Bromotri(pyrrolidino)phosphonium hexafluorophosphate, 200.0 mg, 0.0004318 mol) and triethylamine (0.093 mL, 0.00067 mol) and tetrahydrofuran (5.0 mL, 0.062 mol) and N,N-dimethylformamide (10.0 mL, 0.129 mol) and methylene chloride (5.0 mL, 0.078 mol) under an atmosphere of Nitrogen. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with biotage to give product 19 (15 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07504509B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-d4fb084fa70a4477a98bdbf348bba5d8 |
| Source note | uspto-grants-2009_03 |