Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 59316726 | HCID 59316726 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59316747 | HCID 59316747 | 36% |
Reaction Steps
To a solution of ethyl 4-(4-bromo-1H-indazol-1-yl)-2,2-dimethylbutanoate (D112) (600 mg, 1.77 mmol) and Zn(CN)2 (207 mg, 1.77 mmol) in DMF (5 ml) at room temperature was added Pd(PPh3)4 (204 mg, 0.18 mmol) and the resulting mixture was stirred at 100° C. over the weekend, heated for a further 5 hours and then cooled to room temperature and diluted with AcOEt. The organic phase was filtered through celite and washed with water then brine, dried and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [10-20% EtOAc/cyclohexane] gave the title compound (200 mg, 36%) as a colourless oil. MS (ES) C16H19N3O2 requires 285, found 286 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08324254B2 |
|---|
| Source dataset | uspto-grants-2012_12 |
|---|
| ORD ID | ord-27cb0a3f63ac452fa8a1a777b72b6245 |
|---|
| Source note | uspto-grants-2012_12 |
|---|