Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 2-Acetoxyphenylboronic acid pinacol ester | HCID 2774001 | — |
| Reactant | 7-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine | HCID 57416128 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 136360287 | HCID 136360287 | 92% |
Reaction Steps
Into a 8-dram vial, Palladium Acetate (0.050 g, 0.022 mol) and Triphenylphosphine (0.16 g, 0.063 mmol) were added. The mixture was purged under an atmosphere of Nitrogen for 10 minutes. 1,4-Dioxane (17.1 mL,) was added and stirred for 10 minutes at room temperature. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.550 g, 2.25 mmol), Acetic acid 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl ester (1.18 g, 4.51 mmol), N,N-Dimethylformamide (34 mL), and 1.50 M of Sodium carbonate in Water (13.5 mL, 0.0203 mol) were added. The reaction was heated at 90° C. for 18 hours. The reaction was partitioned with water and stirred at room temperature for 2 hours. The solid was filtered and washed with water. The resulting yellow solid was dried under vacuum to give 2-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (0.53 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08471005B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-13663a3ff9e74c70b2f430a6df06014c |
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| Source note | uspto-grants-2013_06 |
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