Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 2758015 | — |
| Reactant | HCID 71512056 | HCID 71512056 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 89561194 | HCID 89561194 | 49.1% |
Reaction Steps
2-Chloro-5-iodo-N-methylpyridin-4-amine (Intermediate I-8) (30 mg, 0.112 mmol), tetrakis(triphenylphosphine) palladium (0) (6.5 mg, 5.59 μmol) and 0.5 M aqueous sodium carbonate solution (290 μL, 0.145 mmol) were added to 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61 μL, 0.335 mmol) in MeCN. The mixture was heated at 130° C. in a microwave reactor for 1 hour. The mixture was concentrated in vacuo. Preparative thin layer chromatography, eluting with 1% NH3, 6% MeOH in CH2O12, gave 2-chloro-5-cyclopropyl-N-methylpyridin-4-amine (10 mg, 0.055 mmol, 49% yield) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09403797B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-167ed020ba324db38c799eda6cbc31ab |
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| Source note | uspto-grants-2016_08 |
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