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CAS 109-04-6
2-bromopyridine
Codes: REMIB-002, COBI-023, ATAZ-003, VISM-014
Application context (from source-drug indications)
SedationRemimazolam BesilateAnaesthesiaRemimazolam BesilateMelanomaCobimetinib FumarateHIV infectionAtazanavir Sulfate/CobicistatBasal cell carcinomaVismodegibMultiple myelomaVismodegibLymphomaVismodegibSolid tumourVismodegibHaematological malignancyVismodegibMesenchymal chondrosarcomaVismodegibHIV infectionAtazanavir SulfateAcquired immunodeficiency syndromeAtazanavir SulfateMycobacterium tuberculosis infectionAtazanavir SulfateType 1 diabetesAtazanavir Sulfate
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Remimazolam Besilate | Tier C — Watch / trade | 2030 |
| Cobimetinib Fumarate | Tier C — Watch / trade | 2029 |
| Atazanavir Sulfate/Cobicistat | Tier C — Watch / trade | - |
| Vismodegib | Tier C — Watch / trade | - |
| Atazanavir Sulfate | Tier B — Position early | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
2-amino-5-bromobenzoic acid→2-bromopyridine→(2-amino-5-bromophenyl)(pyridin-2-yl)methanone→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid→methyl (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-bromo-2-picolinoylphenyl)amino)-5-oxopentanoate→methyl (S)-3-(7-bromo-2-oxo-5-(pyridin-2-yl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoate→dimorpholinophosphinic chloride→methyl (S)-3-(7-bromo-2-((dimorpholinophosphoryl)oxy)-5-(pyridin-2-yl)-3H-benzo[e][1,4]diazepin-3-yl)propanoate→1-aminopropan-2-ol→methyl 3-((3S)-7-bromo-2-((2-hydroxypropyl)amino)-5-(pyridin-2-yl)-3H-benzo[e][1,4]diazepin-3-yl)propanoate
(S)-tert-butyl 2-(1-(3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoyl)-3-hydroxyazetidin-3-yl)piperidine-1-carboxylate→tert-butyl 3-oxoazetidine-1-carboxylate→2-bromopyridine→tert-butyl 3-hydroxy-3-(pyridin-2-yl)azetidine-1-carboxylate→COBI-025→2,2,2-trifluoro-1-(3-hydroxy-3-(pyridin-2-yl)azetidin-1-yl)ethanone hydrochloride→2,2,2-trifluoro-1-(3-hydroxy-3-(piperidin-2-yl)azetidin-1-yl)ethanone hydrochloride→tert-butyl 2-(3-hydroxy-1-(2,2,2-trifluoroacetyl)azetidin-3-yl)piperidine-1-carboxylate→tert-butyl 2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate→3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoyl chloride
4-bromobenzaldehyde→1-bromo-4-(dimethoxymethyl)benzene→2-bromopyridine→4-(pyridin-2-yl)benzaldehyde→tert-butyl hydrazinecarboxylate→tert-butyl (E)-2-(4-(pyridin-2-yl)benzylidene)hydrazine-1-carboxylate→tert-butyl 2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→tert-butyl ((S)-1-((R)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl 2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol→(S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoic acid
2-bromopyridine→4-(pyridin-2-yl)benzaldehyde→tert-butyl hydrazinecarboxylate→tert-butyl (E)-2-(4-(pyridin-2-yl)benzylidene)hydrazine-1-carboxylate→tert-butyl 2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→tert-butyl ((S)-1-((R)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl 2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol→(S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoic acid→(4-formylphenyl)boronic acid→tert-butyl ((2S,3R)-3,4-dihydroxy-1-phenylbutan-2-yl)carbamate→(6R,7S)-7-benzyl-2,2,3,3,11,11-hexamethyl-9-oxo-4,10-dioxa-8-aza-3-siladodecan-6-yl methanesulfonate→(2R,3S)-3-((tert-butoxycarbonyl)amino)-1-hydroxy-4-phenylbutan-2-yl methanesulfonate
2-chloro-4-(methylsulfonyl)benzoyl chloride→4-chlorobenzoic acid→4-chloro-3-iodobenzoic acid→tert-butyl (4-chloro-3-iodophenyl)carbamate→4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)→tert-butyl (4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate→2-bromopyridine→tert-butyl (4-chloro-3-(pyridin-2-yl)phenyl)carbamate→4-chloro-3-(pyridin-2-yl)aniline
4-bromobenzaldehyde→1-bromo-4-(dimethoxymethyl)benzene→2-bromopyridine→4-(pyridin-2-yl)benzaldehyde→tert-butyl hydrazinecarboxylate→tert-butyl (E)-2-(4-(pyridin-2-yl)benzylidene)hydrazine-1-carboxylate→tert-butyl 2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→tert-butyl ((S)-1-((R)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl 2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol→(S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoic acid
2-bromopyridine→4-(pyridin-2-yl)benzaldehyde→tert-butyl hydrazinecarboxylate→tert-butyl (E)-2-(4-(pyridin-2-yl)benzylidene)hydrazine-1-carboxylate→tert-butyl 2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→tert-butyl ((S)-1-((R)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl 2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazine-1-carboxylate→(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol→(S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoic acid→(4-formylphenyl)boronic acid→tert-butyl ((2S,3R)-3,4-dihydroxy-1-phenylbutan-2-yl)carbamate→(6R,7S)-7-benzyl-2,2,3,3,11,11-hexamethyl-9-oxo-4,10-dioxa-8-aza-3-siladodecan-6-yl methanesulfonate→(2R,3S)-3-((tert-butoxycarbonyl)amino)-1-hydroxy-4-phenylbutan-2-yl methanesulfonate
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