Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 3-Tolylboronic acid | HCID 2733950 | — |
| Reactant | HCID 87364079 | HCID 87364079 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67343116 | HCID 67343116 | 72.3% |
Reaction Steps
To the title compound of Step A (0.12 g, 0.27 mmol), 3-methylphenylboronic acid (0.08 g, 0.60 mmol), K3PO4 (0.128 g, 0.54 mmol), Pd(dppf)Cl2.CH2Cl2 (0.013 g, 0.017 mmol) and dppf (0.006 g, 0.010 mmol) was added dioxane (3 mL). The flask was heated at 100° C. for 18 h, cooled to rt, diluted with EtOAc and filtered through a small silica pad. Silica gel chromatography (10-40% EtOAc in hexanes) gave 0.073 g (72% yield) of the title compound. 1H NMR (CDCl3): 7.31-7.26 (m, 4H), 7.18-7.15 (m, 1H), 7.05 (dd, J=8.2, 2.0 Hz, 1H), 6.57 (d, J=1.9 Hz, 1H), 4.86-4.81 (m, 1H), 4.30-4.26 (m, 2H), 3.96 (dd, J=10.2, 4.2 Hz, 2H), 2.40 (s, 3H), 1.44 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08575364B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-e878a5fe966646bcb1392e625e0e6ab5 |
|---|
| Source note | uspto-grants-2013_11 |
|---|
