Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Vinyl ether | HCID 8024 | — |
| Reactant | HCID 53442856 | HCID 53442856 | — |
| Reactant | HCID 86661507 | HCID 86661507 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1H-Indazole | HCID 9221 | 78% |
Reaction Steps
To a mixture of bromide (5b) and pinacol vinylboronate (6, 1.2 equiv) in DMF was added LiOH (3 equiv) followed by PdCl2(dppf).CH2Cl2 (3 mol %). The reaction mixture was heated to 70° C. and stirred for 18 h. HPLC analysis indicated complete conversion to the vinylether intermediate. After cooling the reaction mixture to 50° C., HCl (25%) was added and the mixture was stirred at this temperature for 1 h. The reaction was complete at this point. After workup, compound 8 was isolated as a crystalline solid in 78% yield. MS (Turbo Spray): 231 (35%), 229 (M+H+, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08779150B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-e493a866801b44fb9822831b44550bdf |
|---|
| Source note | uspto-grants-2014_07 |
|---|
