Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(1H-Imidazol-1-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 45785898 | — |
| Reactant | N-(5-Iodo-4-methyl-2-thiazolyl)acetamide | HCID 57417074 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 57417075 | HCID 57417075 | — |
Reaction Steps
A mixture of N-(5-iodo-4-methyl-thiazol-2-yl)-acetamide (312 mg), 6-(imidazol-1-yl)pyridine-2-boronic acid pinacol ester (600 mg), 1,1′-bis(diphenylphosphino)ferrocene-dichloropalladium (II) (45 mg) and sodium carbonate (594 mg) in DME (3.1 ml) and water (3.1 ml) is heated in a Emrys Optimiser personal chemistry microwave at 85° C. for 45 minutes. Water is added (5 ml) and the mixture extracted with 3×10% methanol in CH2Cl2, the combined organic layers evaporated and purified by reversed phase chromatography (Method B) collecting the 12.8 minute retention time component. Partial evaporation of the fractions, neutralization with NaHCO3, extraction with 10% methanol in CH2Cl2 (5×) and evaporation gives a white solid. Further purification of this material by normal phase chromatography on silica gel eluting with a gradient from EtOAc to 10% methanol in EtOAc gives the title compound as a white solid. Hplc/MS (Method C) RT 1.31 minutes, M+H 299.9 and M−H 298.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08940771B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-f7db861608a747388f0ee1b1c1772c36 |
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| Source note | uspto-grants-2015_01 |
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