HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 10022054, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 11724985 | HCID 11724985 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Phosphorus oxychloride | HCID 24813 | — |
| Solvent | Chloroform isopropyl alcohol | HCID 21906603 | — |
| Product | HCID 10022054 | HCID 10022054 | 59% |
Reaction Steps
Reflux 7-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-quinoxalin-2-one (Example 55b; 20 mg, 0.055 mmol,) in POCl3 overnight. After removing POCl3, treat the residue with Zn(CN)2 (11.6 mg, 0.11 mmol) and Pd(PPh3)4 (3 mg, 0.003 mmol) in DMF (1 mL) at 100° C. for 20 min in microwave. Cool the solution to room temperature, dilute with chloroform/isopropyl alcohol and wash with brine. Dry the solution over sodium sulfate, filter, and evaporate the solvents to give a viscous mixture. Purify the crude product by column chromatography eluting with a gradient from dichloromethane to 10% methanol in dichloromethane to give the desired compound 12 mg (59%). MS (electrospray, m/z) 371.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07405299B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-71860f4ea0c14fa787d70122af074dc3 |
| Source note | uspto-grants-2008_07 |