Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 1-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea | HCID 44235257 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Abt-116 | HCID 46890602 | — |
Reaction Steps
A mixture of Example 3A (5.12 g, 16.9 mmol), Example 2C (3.78 g, 17.9 mmol), Pd2 dba3:CHCl3 (264 mg, 0.255 mmol), xantphos (442 mg, 0.764 mmol), and Cs2CO3 (8.28 g, 25.4 mmol) in dioxane (60 mL) was flushed with N2 and stirred at 90° C. for 16 hours. The mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed sequentially with water and brine, and purified by flash chromatography (0 to 35% ethyl acetate/dichloromethane) to provide the title compound. 1H-NMR (DMSO-d6) δ 8.82 (s, 1H), 8.05 (s, 1H), 7.64 (d, 1H), 7.50-7.53 (m, 3H), 7.20 (t, 1H), 7.14 (d, 1H), 6.81 (t, 1H), 4.45 (d, 2H), 4.00 (s, 3H), 2.70 (ddd, 2H), 1.45 (ddd, 2H), 0.97 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08815930B2 |
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| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-9f8551f0f8b647a295c291568c412923 |
|---|
| Source note | uspto-grants-2014_08 |
|---|
