Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-(Methoxycarbonyl)pyridine-3-boronic acid | HCID 45588187 | — |
| Reactant | HCID 86709420 | HCID 86709420 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 86709421 | HCID 86709421 | 87% |
Reaction Steps
5-(((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)pyrazine-2-carbonitrile (for a preparation, see Intermediate 51) (390 mg, 1.010 mmol), (6-(methoxycarbonyl)pyridin-3-yl)boronic acid (219 mg, 1.21 mmol), PdCl2(dppf) (111 mg, 0.151 mmol) and triethylamine (0.281 ml, 2.02 mmol) were combined in a mixture of dry MeOH (6 mL) and DME (1 mL). The mixture was heated under microwave irradiation to 120° C. for 45 mins. The mixture was then concentrated in vacuo and the residue purified by chromatography (100 g column, EtOAc/cyclohexane gradient) to give methyl 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinate (389 mg, 0.879 mmol, 87% yield) as a pink solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08993554B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-807225cb182a41faa98fa628368f2268 |
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| Source note | uspto-grants-2015_03 |
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