Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Cyanophenylboronic acid | HCID 2734325 | — |
| Reactant | HCID 86657448 | HCID 86657448 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67385834 | HCID 67385834 | 50.5% |
Reaction Steps
To a solution of 2-amino-6′-bromo-1-methyl-2′-phenylspiro[imidazole-4,4′-thiochroman]-5(1H)-one TFA salt (70 mg, 0.14 mmol), 3-cyanophenylboronic acid (51 mg, 0.34 mmol), and Cs2CO3 (250 mg) in 1,4-dioxane (4 mL) and H2O (0.5 mL) charged in a 10 mL CEM microwave test tube is added PdCl2(PPh3)2 (20 mg). Then the system is degassed by sweeping with N2. The tube is capped and heated to 110° C. for 30 min in a CEM microwave reactor. Solvent is removed in vacuo and the residue is purified by preparative HPLC to give 3-(2-amino-1-methyl-5-oxo-2′-phenyl-1,5-dihydrospiro-[imidazole-4,4′-thiochroman]-6′-yl)benzonitrile (30 mg) as a TFA salt. MS ESI+ve m/z 425 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921359B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-f321c554285245e8bc6e60f41561e179 |
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| Source note | uspto-grants-2014_12 |
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