Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium | HCID 223 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | HCID 59332714 | HCID 59332714 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 66746783 | HCID 66746783 | — |
Reaction Steps
5-Bromo-3-(1,1-dioxido-2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (100 mg, 0.224 mmol) was placed in a microwave vial and combined with 1,4-Dioxane (3 mL) and Water (1.5 mL). Argon was bubbled through the mixture for 10 mins, stirring and then PdCl2(dppf) (8.18 mg, 0.011 mmol) was added, and argon was bubbled another 10 mins. The vial was sealed and put under microwave 5 mins at 100° C. with high absorption parameter. The crude was evaporated to remove the most of the dioxane. Then it was partitioned between EtOAc and water. Organic layer was dried over magnesium sulfate and solvent removed under vacuum to afford 155 mg of crude material as a gummy brown oil which was dissolved in 1-2 mL of DMSO, and run through the ammonium Gilson to afford 17 mg of (racemic)-3-(1,1-dioxido-2-phenyltetrahydro-2H-thiopyran-4-yl)-5-phenyl-1H-indole-7-carboxamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08071584B2 |
|---|
| Source dataset | uspto-grants-2011_12 |
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| ORD ID | ord-5478bfa78c4243a8bc628166550add02 |
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| Source note | uspto-grants-2011_12 |
|---|
