Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Bromo-5-(trifluoromethyl)pyridine | HCID 2736434 | — |
| Reactant | HCID 86628826 | HCID 86628826 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86628825 | HCID 86628825 | — |
Reaction Steps
A mixture of 3-formyl-1-(4-isopropoxyphenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)indole-2-carboxylic acid ethyl ester (600 mg, 1.26 mmol; see step (a) above), 2-bromo-5-(trifluoromethyl)pyridine (426 mg, 1.89 mmol), Na2CO3 (aq, 2 M, 1.89 mL, 3.78 mmol), Pd(PPh3)4 (70 mg, 0.06 mmol), EtOH (5 mL) and toluene (20 mL) was heated at 80° C. for 24 h, allowed to cool, poured into H2O and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 500 mg (80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08097623B2 |
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| Source dataset | uspto-grants-2012_01 |
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| ORD ID | ord-f6776f09621b424f92ae8630477411ae |
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| Source note | uspto-grants-2012_01 |
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