Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 56850539 | HCID 56850539 | — |
| Reactant | HCID 58506151 | HCID 58506151 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 135887207 | HCID 135887207 | 16.1% |
Reaction Steps
To a solution of 5-Bromo-l-methyl-1H-pyrazole-3-carboxylic acid(pyridin-4-ylmethyl)-amide (90 mg, 0.3 mmol), and 2-(3-Methyl-1,2,4-oxadiazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester (142 mg, 0.33 mmol) in N,N dimethylformamide (1.5 ml) is added aqueous Na2CO3 (0.4 ml, 0.77 mmol). The mixture is purged with argon for 10 minutes. (Bis(di-t-butyl(4-dimethylaminutesophenyl)phosphine)dichloropalladium(II) (40 mg, 0.06 mmol), is then added and the reaction mixture is sealed in a seal tube and heated to 100° C. in a microwave reactor for 30 minutes. The reaction mixture is diluted with ethyl acetate (70 ml), washed with water (20 ml), brine (2×25 ml), dried over Na2SO4, filtered, and concentrated in vacuo. Purified by reverse phase LC/MS to provide the title compound 20 mg, (16%), LC/MS ESI m/z (M+H)+=414.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785489B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-172ef942ad374de4b52d7eae43f632ce |
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| Source note | uspto-grants-2014_07 |
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