Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-(1,3,2-Dioxaborinan-2-yl)pyridine | HCID 4198005 | — |
| Reactant | 7-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile | HCID 59198465 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59198493 | HCID 59198493 | — |
Reaction Steps
To a suspension of 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9) in DMF (0.1 M) were added the pyridine-3-boronic acid 1,3-propanediol cyclic ester (1.5 equiv), 2 M Na2CO3 (3 equiv) and PdCl2dppf (0.05 equiv). The mixture was heated in the microwave reactor at 110° C. for 10 min. The reaction mixture was partitioned between EtOAc and saturated NaHCO3. The organic phase was separated, dried over MgSO4, filtered, evaporated and purified by flash chromatography (70:30 hexanes/EtOAc to 100% EtOAc) to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08518964B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-99b5f753f053439b8c1b9ab0d5938148 |
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| Source note | uspto-grants-2013_08 |
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