Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 67019901 | HCID 67019901 | — |
| Catalyst | Water | HCID 962 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Product | HCID 24993727 | HCID 24993727 | — |
Reaction Steps
To a suspension of the product of Step A (141 mg, 0.25 mmol), Zn(CN)2 (29.4 mg, 0.25 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (5.2 mg, 0.005 mmol), and dppf (6.9 mg, 0.01 mmol) in 5.0 mL of DMF was added one drop of H2O. The solution was degassed and stirred at 120° C. for 16 h, the reaction mixture was cooled to rt and diluted with EtOAc (20 mL). The solid was filtered off and washed with EtOAc. The filtrate was concentrated and chromatography on a Biotage 40+M cartridge using 2:3 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.27 (s, 9H), 1.48 (s, 3H), 1.56 (s, 3H), 1.84 (m, 1H), 2.26 (m, 1H), 5.50 (m, 1H), 5.82 (br. s, 1H), 6.95 (d, J=8.2, 2H), 7.19 (d, J=8.3, 2H), 7.41-7.58 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07999107B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-2783e51eead1425fa5ca611eb9a86775 |
|---|
| Source note | uspto-grants-2011_08 |
|---|
