HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → HCID 178504206, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile | HCID 58266668 | — |
| Catalyst | Water | HCID 962 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178504206 | HCID 178504206 | — |
Reaction Steps
To a solution of 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (100 mg, 0.3 mmol) in tetrahydrofuran (1.8 mL) was added sodium hydride as a 60% dispersion in mineral oil (22 mg, 0.56 mmol) followed by a few drops of water. The reaction mixture was stirred at ambient temperature for 5 minutes and then at 40° C. for 2 hours. The mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 5-100% ethyl acetate in heptane) to afford the title compound as a pale yellow oil, which was used in the next step without any further purification (70 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09440976B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-5b20dbe7f77841dfa75b1479d2b1f97e |
| Source note | uspto-grants-2016_09 |