Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Propyn-1-ol, 3-(trimethylsilyl)- | HCID 78930 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 1-[2'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-5'-iodo-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one | HCID 58386754 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58386693 | HCID 58386693 | — |
Reaction Steps
Under an argon atmosphere 44 mg (0.34 mmol) 3-trimethylsilanyl-prop-2-yn-1-ol, 50 μL TEA, 13 mg 1,1′-bis(diphenylphosphine)ferrocene dichloropalladium (II) and 3 mg (20 μmol) copper(I) iodide were added to 0.10 g (0.17 mmol) 1-[2′-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-5′-iodo-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 4.0 mL 1,4-dioxane. Then 0.36 mL (0.36 mmol) of a 1 molar tetrabutylammonium fluoride solution in THF were added dropwise and the mixture was then stirred for 4 h at 80° C. The reaction mixture was mixed with water and the precipitate formed was suction filtered. The precipitate was stirred in 6 mL DMF and suction filtered. The filtrate was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08829006B2 |
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| Source dataset | uspto-grants-2014_09 |
|---|
| ORD ID | ord-5c313052bd85448db9a0437b0f8e8a0b |
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| Source note | uspto-grants-2014_09 |
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