2-(Bis(tert-butoxycarbonyl)amino)-5-bromopyridin-3-yl 4-methylbenzenesulfonate
This compound (CAS 1803573-21-8), named 2-(bis(tert-butoxycarbonyl)amino)-5-bromopyridin-3-yl 4-methylbenzenesulfonate or imidodicarbonic acid 2-[5-bromo-3-[[(4-methylphenyl)sulfonyl]oxy]-2-pyridinyl]-, 1,3-bis(1,1-dimethylethyl) ester, is a heavily functionalised pyridine building block supplied as a solid at 98 percent purity for laboratory and manufacturing use. Three reactive sites coexist in the molecule: an aryl bromide, a tosylate ester and two acid-labile tert-butoxycarbonyl groups, so it must be stored dry, cool and away from light, strong nucleophiles and bases. The bromine enables cross-coupling, the tosylate is a leaving group for substitution, and the bis-Boc protected amine can be unveiled selectively with acid, making the compound valuable for late-stage diversification and analogue library construction.
1. Pharmaceutical intermediate: a versatile advanced building block for constructing pyridine-containing kinase inhibitors, antibiotics, antivirals and other drug candidates in discovery, process development and scale-up chemistry.
2. Orthogonal reactivity: the aryl bromide supports Suzuki, Buchwald-Hartwig, Stille, Negishi and related couplings, the tosylate allows nucleophilic displacement by amines and thiols, and the bis-Boc amine is deprotected selectively under acidic conditions.
3. Medicinal chemistry applications: used to introduce substituted aminopyridine motifs that tune basicity, solubility, hydrogen bonding and target binding in structure-activity studies, fragment elaboration and parallel library synthesis.
4. Handling and storage: keep in a sealed container in a cool, dry place protected from light; the tosylate is a potential alkylating group and the Boc groups release carbon dioxide and isobutylene on acid treatment, so handle with appropriate containment, ventilation and protective equipment.
Product Name: 2-(Bis(tert-butoxycarbonyl)amino)-5-bromopyridin-3-yl 4-methylbenzenesulfonate
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