Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | tert-Butyl isocyanate | HCID 62412 | — |
| Reactant | 3,5-Dibromo-4-methylpyridine | HCID 819338 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 69072763 | HCID 69072763 | — |
Reaction Steps
Under argon, an n-butyllithium solution in hexane (1.55N, 6.6 ml) is added dropwise to a solution of 3,5-dibromo-4-methylpyridine (intermediate 10.1, 2.51 g, 10 mmol) kept at −100° C. After stirring for 10 min, tert-butyl isocyanate (2.28 ml, 20 mmol) is added. The stirring is maintained for 20 min at −100° C. and then for 1 h at −78° C. and at room temperature overnight. An aqueous NH4Cl solution is added to the reaction mixture. Extraction with AcOEt/H2O gives a brown solid which is taken up in an AcOEt/petroleum ether mixture. The compound obtained is isolated by filtration.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07482342B2 |
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| Source dataset | uspto-grants-2009_01 |
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| ORD ID | ord-797dc3b8945d4f4ea7760241cb3fd620 |
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| Source note | uspto-grants-2009_01 |
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