Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 86729570 | HCID 86729570 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 86729569 | HCID 86729569 | 43% |
Reaction Steps
To a stirred solution of 16-2 (639 mg, 1.67 mmol), and zinc cyanide (98 mg, 0.84 mmol) in DMF (6 mL) under nitrogen was added Pd2(dba)3 (76 mg, 0.08 mmol) and DPPF (93 mg, 0.17 mmol) and the resulting mixture was heated to 120° C. for 90 minutes. The reaction was allowed to cool and partititioned between ethyl acetate and a saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 10-100% ethyl acetate/hexane gradient gave 16-3 as a solid (200 mg, 43%). MS (ES) (M+H)+: observed=282.2, calculated=282.7.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062059B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-a5bd663b78da42649a690639de846aa6 |
|---|
| Source note | uspto-grants-2015_06 |
|---|
