30766-11-1

Basic information

• Product Name: 5-Bromopyridine-2-carboxylic acid
• Synonyms: METHYL 5-BROMOPICOLINATE;METHYL 5-BROMO-2-PYRIDINECARBOXYLATE;5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER;5-bromo-2-pyridine carboxlic acid;5-bromo-2-pyridinecarboxlic acid;5-Bromopyridine-2-carboxylic acid;5-BROMO-2-PICOLINIC ACID5-BROMO-2-PYRIDINECARBOXYLIC ACID;5-Bromo-2-pyridinecaroboxylic acid
• CAS NO: 30766-11-1
• Molecular Formula: C₆H₄BrNO₂
• Molecular Weight: 202.00546
• EINECS: -0
• Product Categories: blocks;Bromides;Carboxes;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Carboxylic Acids;Pyridine Series;Carboxy;Organohalides;Bromopyridines;Halopyridines;Carboxylic Acids
• Mol File: 30766-11-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 173-175°C
• Boiling Point: 319.5 °C at 760 mmHg
• Flash Point: 147 °C
• Appearance: White to off-white/Powder
• Density: 1.813 g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• PKA: 3.41±0.10(Predicted)
• CAS DataBase Reference: 5-Bromopyridine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromopyridine-2-carboxylic acid(30766-11-1)
• EPA Substance Registry System: 5-Bromopyridine-2-carboxylic acid(30766-11-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 30766-11-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 30766-11-1 differently. You can refer to the following data:
1. 5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate. Store in cool, dry place in a well sealed container. Store away from oxidizing agents.
2. 5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate.

Chemical Properties

white Cryst

InChI:InChI=1/C6H4BrNO2/c7-4-1-2-5(6(9)10)8-3-4/h1-3H,(H,9,10)/p-1

Synthetic route

tert-butyl 5-bromopyridine-2-carboxylate (845306-08-3) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
In hexafluoropropan-2-ol at 100℃; for 3h; Microwave irradiation;	95%

methyl 5-bromopicolinate (29682-15-3) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 15h;	90%
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃;
With sodium hydroxide In water at 20℃; for 12h;

2,5-dibromopyridine (624-28-2) + carbon dioxide (124-38-9) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With n-butyllithium In hexane; toluene at -75℃; for 2h;	64%
Stage #1: 2,5-dibromopyridine With n-butyllithium In toluene at -78℃; for 2h; Stage #2: carbon dioxide In toluene at -78℃; for 1h; Stage #3: With hydrogenchloride In water; toluene	47%
Stage #1: 2,5-dibromopyridine With n-butyllithium In toluene at -78℃; for 2h; Stage #2: carbon dioxide In toluene at -78℃; for 1h;	47%

2-Cyano-5-bromopyridine (97483-77-7) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With hydrogenchloride In water Reflux;	64%
With hydrogenchloride for 24h; Heating;
Stage #1: 2-Cyano-5-bromopyridine With potassium hydroxide; ethanol; water at 80℃; for 24h; Stage #2: With hydrogenchloride; water pH=4;

5-bromo-2-methylpyridine (3430-13-5) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With potassium permanganate In water at 80℃;	39%
With potassium permanganate
With potassium permanganate; water at 100℃; for 6h;
With potassium permanganate Heating;

5-amino-pyridine-2-carboxylic acid (24242-20-4) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With hydrogen sulfide; hydrogen bromide; urea; copper(I) bromide; sodium nitrite 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux; Yield given. Multistep reaction;

5-nitro-pyridin-2-ylamine (4214-76-0) → 5-bromoisonicotinic acid (30766-11-1)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) 48 percent HBr, Br2; 2.) NaNO2 / 1) 30-40 deg C; 2) -5 deg C, H2O; 10-15 Deg C, 90 min.; 3) 40 deg C. 15 min 2: dimethylsulfoxide / 0.08 h / 180 °C 3: 54 percent / HCl / 1.5 h / Heating 4: 70 percent / H2S, 25 percent NH3 5: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme

2-bromo-5-nitropyridine (4487-59-6) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylsulfoxide / 0.08 h / 180 °C 2: 54 percent / HCl / 1.5 h / Heating 3: 70 percent / H2S, 25 percent NH3 4: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme

5-nitropyridine-2-carbonitrile (100367-55-3) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 54 percent / HCl / 1.5 h / Heating 2: 70 percent / H2S, 25 percent NH3 3: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme

5-nitropicolinic acid (30651-24-2) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / H2S, 25 percent NH3 2: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme

5-Amino-2-methylpyridine (80287-53-2, 3430-14-6) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 2: aqueous KMnO4 View Scheme

6-methylnicotinamide (6960-22-1) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOCl; aqueous KOH 2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 3: aqueous KMnO4 View Scheme

ethyl 6-methylnicotinate (21684-59-3) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: aqueous NH3 2: NaOCl; aqueous KOH 3: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 4: aqueous KMnO4 View Scheme
Multi-step reaction with 6 steps 1: N2H4+H2O 2: KNO2; aqueous HCl 4: aqueous KOH 5: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 6: aqueous KMnO4 View Scheme

6-methylpyridine-3-carbohydrazide (197079-25-7) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: KNO2; aqueous HCl 3: aqueous KOH 4: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 5: aqueous KMnO4 View Scheme

6-methyl-nicotinoyl azide (64038-04-6) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 4 steps 2: aqueous KOH 3: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 4: aqueous KMnO4 View Scheme

(6-methyl-[3]pyridyl)-carbamic acid ethyl ester (247077-42-5) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous KOH 2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 3: aqueous KMnO4 View Scheme

1,3-bis(6-methylpyridin-3-yl)urea (858844-85-6) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated aqueous HCl / 130 °C 2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 3: aqueous KMnO4 View Scheme

C6H3BrNO2(1-)*Na(1+) (108885-80-9) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With water; acetic acid at 25℃; for 16h;

5-bromo-pyridine-2-carbaldehyde (31181-90-5) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Stage #1: 5-bromo-pyridine-2-carbaldehyde With potassium permanganate; sodium carbonate In water at 10 - 20℃; Stage #2: With hydrogenchloride In water pH=2 - 4;
With 1,4-dithio-D,L-threitol; recombinant aldehyde dehydrogenase from Escherichia coli; water‐forming NADH oxidase from Streptococcus mutans; NAD In aq. phosphate buffer at 40℃; for 4h; pH=8.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; chemoselective reaction;

2,5-dibromopyridine (624-28-2) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethylsilylmethyllithium / toluene / 0.5 h / -78 - 0 °C 1.2: 3 h 1.3: 18 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran / 15 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: trimethylsilylmethyllithium / toluene / 0.5 h / -78 - 0 °C 1.2: 3 h 1.3: 18 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran / 15 h / 0 - 20 °C View Scheme

5-bromo-pyridine-2-carboxylic acid ethyl ester (77199-09-8) → 5-bromoisonicotinic acid (30766-11-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 15h;

5-bromoisonicotinic acid (30766-11-1) + ethanol (64-17-5) → 5-bromo-pyridine-2-carboxylic acid ethyl ester (77199-09-8)

Conditions	Yield
With thionyl chloride at 20℃; for 18h;	100%
With sulfuric acid at 75℃; for 2h;	86%
Stage #1: 5-bromoisonicotinic acid With thionyl chloride for 2h; Heating / reflux; Stage #2: ethanol In toluene Heating / reflux; Stage #3: With sodium carbonate In water; toluene pH=8;	28%

5-bromoisonicotinic acid (30766-11-1) → 5-bromopyridine-2-carbonyl chloride (137178-88-2)

Conditions	Yield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	100%
With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 2h;	99%
With thionyl chloride for 2h; Inert atmosphere; Reflux;	93%

5-bromoisonicotinic acid (30766-11-1) → 5-bromo-2-carboxypyridin-1-ium-1-olate (959741-37-8)

Conditions	Yield
Stage #1: 5-bromoisonicotinic acid With urea hydrogen peroxide adduct; trifluoroacetic anhydride In acetonitrile at 0℃; for 4.5h; Stage #2: With sodium thiosulfate In water; acetonitrile at 0℃; for 0.166667h;	100%
Stage #1: 5-bromoisonicotinic acid With urea hydrogen peroxide adduct; trifluoroacetic anhydride In acetonitrile at 0℃; for 4.5h; Stage #2: With sodium thiosulfate In water; acetonitrile for 0.166667h;
With dihydrogen peroxide; urea; trifluoroacetic anhydride In acetonitrile at 0℃; for 0.5h;	19.6 g
With dihydrogen peroxide; urea; trifluoroacetic anhydride In acetonitrile at 0℃; for 0.5h;	19.6 g
Stage #1: 5-bromoisonicotinic acid With urea hydrogen peroxide adduct In acetonitrile at 0℃; for 0.333333h; Stage #2: With trifluoroacetic anhydride In acetonitrile at 20℃;

5-bromoisonicotinic acid (30766-11-1) + tert-butyl 4-[6-(dimethoxyboryl)-4H-1,3-benzodioxin-2-yl]piperidine-1-carboxylate (1200575-98-9) → 5-{2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-4H-1,3-benzodioxin-6-yl}pyridine-2-carboxylic acid (1200575-99-0)

Conditions	Yield
With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; acetonitrile at 160℃; for 0.333333h; Irradiation;	100%

5-bromoisonicotinic acid (30766-11-1) + caudatin → C34H44BrNO8

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	100%

5-bromoisonicotinic acid (30766-11-1) + ethyl 2-(furan-2-yl)-5-(trifluoromethyl)piperidine-3-carboxylate → ethyl 1-(5-bromopyridine-2-carbonyl)-2-(furan-2-yl)-5-(trifluoromethyl)piperidine-3-carboxylate

Conditions	Yield
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: ethyl 2-(furan-2-yl)-5-(trifluoromethyl)piperidine-3-carboxylate With triethylamine In dichloromethane at 0 - 20℃;	99%

5-bromoisonicotinic acid (30766-11-1) + 2,3,4,5,6-pentafluorophenol (771-61-9) → (2,3,4,5,6-pentafluorophenyl)-5-bromopyridine-2-carboxylate

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	98%

5-bromoisonicotinic acid (30766-11-1) + methyl (2R)-pyrrolidine-2-carboxylate (43041-12-9) → C12H13BrN2O3

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	96%

5-bromoisonicotinic acid (30766-11-1) + methyl (2S)-pyrrolidine carboxylate (2577-48-2) → C12H13BrN2O3

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	96%

methanol (67-56-1) + 5-bromoisonicotinic acid (30766-11-1) → C7H6BrNO2*ClH (950848-56-3)

Conditions	Yield
With thionyl chloride at -78 - 20℃; for 16.1667h;	95%

5-bromoisonicotinic acid (30766-11-1) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(5-bromopicolinoyl)piperazine-1-carboxylate

Conditions	Yield
With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 20℃;	95%

5-bromoisonicotinic acid (30766-11-1) + rac-tert-butyl ((2R*,5R*)-5-(5-amino-2-fluorophenyl)-2,5-dimethyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-3-yl)carbamate → rac-tert-butyl ((2R*,5R*)-5-(5-(5-bromopicolinamido)-2-fluorophenyl)-2,5-dimethyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-3-yl)carbamate

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere;	95%

5-bromoisonicotinic acid (30766-11-1) + tri-n-butyl(vinyl)tin (7486-35-3) → 5-vinylpyridine-2-carboxylic acid (45946-64-3)

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20 - 100℃; Inert atmosphere;	94.5%

5-bromoisonicotinic acid (30766-11-1) + 1-ethynyl-3-fluoro-benzene (2561-17-3) → 5-(3-fluoro-phenylethynyl)-pyridine-2-carboxylic acid (1403771-21-0)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In N,N-dimethyl-formamide at 90℃; for 0.75h; Sonogashira Cross-Coupling; Microwave irradiation;	94%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In N,N-dimethyl-formamide at 90℃; for 0.75h; Microwave irradiation;	71%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In N,N-dimethyl-formamide at 90℃; for 0.75h; Sonogashira Cross-Coupling; Inert atmosphere;	65%

5-bromoisonicotinic acid (30766-11-1) + caudatin → 3-O-(5-bromopyridine-2-carbonyl)caudatin (1377496-40-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	93.3%

5-bromoisonicotinic acid (30766-11-1) + 2-methoxyethylamine (109-85-3) → 5-bromo-N-(2-methoxyethyl)picolinamide

Conditions	Yield
Stage #1: 5-bromoisonicotinic acid; 2-methoxyethylamine With pyridine In dichloromethane at 0℃; for 0.166667h; Stage #2: With trichlorophosphate In dichloromethane at 0 - 20℃; for 1h;	93%

5-bromoisonicotinic acid (30766-11-1) + trifluoroethylamine (753-90-2) → C8H6BrF3N2O (1496144-72-9)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	93%

5-bromoisonicotinic acid (30766-11-1) + (R)-[5-(3-aminophenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]carbamic acid tert-butyl ester → (R)-tert-butyl (5-(3-(5-bromopicolinamido)phenyl)-5-methyl-5,6-dihydro-2H-1,4-oxazin-3-yl)carbamate

Conditions	Yield
With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 22℃; for 17h; Inert atmosphere;	93%

5-bromoisonicotinic acid (30766-11-1) → 5-bromo-2-pyridinecarboxamide (90145-48-5)

Conditions	Yield
Stage #1: 5-bromoisonicotinic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 80℃; for 1h; Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 1.5h;	92.4%
With ammonium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	73%
Stage #1: 5-bromoisonicotinic acid With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 0 - 23℃; for 1h; Stage #2: With ammonia In tetrahydrofuran; water at 0℃; for 0.5h;	50%
Stage #1: 5-bromoisonicotinic acid With thionyl chloride for 3h; Reflux; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; Cooling with ice;
Stage #1: 5-bromoisonicotinic acid With thionyl chloride for 3h; Reflux; Stage #2: With ammonia In tetrahydrofuran; water Cooling with ice;	43 g

methanol (67-56-1) + 5-bromoisonicotinic acid (30766-11-1) → methyl 5-bromopicolinate (29682-15-3)

Conditions	Yield
With sulfuric acid at 0 - 70℃; for 6h;	92%
Stage #1: methanol; 5-bromoisonicotinic acid With thionyl chloride at 20℃; for 3h; Reflux; Stage #2: With sodium hydrogencarbonate pH=7;	86.9%
With sulfuric acid for 117h; Reflux;	86%

5-bromoisonicotinic acid (30766-11-1) + tert-butylamine (75-64-9) → 5-bromo-pyridine-2-carboxylic acid tert-butylamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h;	92%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h;	92%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h;	92%

5-bromoisonicotinic acid (30766-11-1) + dimethyl amine (124-40-3) → 5-bromo-2-(N,N-dimethylaminocarbonyl)pyridine (845305-86-4)

Conditions	Yield
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: dimethyl amine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 3h;	91.7%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;
With oxalyl dichloride In dichloromethane at 0 - 40℃; for 1h;
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 16h; Stage #2: dimethyl amine In dichloromethane at 0 - 20℃; for 3h;
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride In dichloromethane at 40℃; for 1h; Stage #2: dimethyl amine With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;

5-bromoisonicotinic acid (30766-11-1) + methoxycarbonylmethylamine (616-34-2) → methyl (5-bromopyridine-2-carbonyl)glycinate (915394-66-0)

Conditions	Yield
With thionyl chloride; N-ethyl-N,N-diisopropylamine	90%

5-bromoisonicotinic acid (30766-11-1) + N,N-diethylethylenediamine (100-36-7) → 5-bromo-N-(2-(diethylamino)ethyl)picolinamide (1285446-04-9)

Conditions	Yield
Stage #1: 5-bromoisonicotinic acid With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 3h; Stage #2: N,N-diethylethylenediamine In N,N-dimethyl-formamide at 20℃; for 2h;	90%

4-ethylpiperazine (5308-25-8) + 5-bromoisonicotinic acid (30766-11-1) → (5-bromopyridin-2-yl)(4-ethylpiperazin-1-yl)methanone

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;	89%

1-(2-hydroxyethyl)piperazine (103-76-4) + 5-bromoisonicotinic acid (30766-11-1) → (5-bromopyridin-2-yl)(4-hydroxyethylpiperazin-1-yl)methanone (910903-54-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;	88%
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	65%

5-bromoisonicotinic acid (30766-11-1) + cyclobutylamine (2516-34-9) → 5-bromo-N-cyclobutylpicolinamide (890928-69-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	88%

Upstream product

• 24242-20-4 5-amino-pyridine-2-carboxylic acid 
• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 4487-59-6 2-bromo-5-nitropyridine 
• 100367-55-3 5-nitropyridine-2-carbonitrile 
• 77199-09-8 5-bromo-pyridine-2-carboxylic acid ethyl ester 
• 29682-15-3 methyl 5-bromopicolinate 
• 624-28-2 2,5-dibromopyridine 
• 845306-08-3 tert-butyl 5-bromopyridine-2-carboxylate 
• 31181-90-5 5-bromo-pyridine-2-carbaldehyde 
• 858844-85-6 1,3-bis(6-methylpyridin-3-yl)urea 
• 247077-42-5 (6-methyl-[3]pyridyl)-carbamic acid ethyl ester 
• 64038-04-6 6-methyl-nicotinoyl azide 
• 197079-25-7 6-methylpyridine-3-carbohydrazide 
• 21684-59-3 ethyl 6-methylnicotinate 

Downstream Products

• 77199-09-8 5-bromo-pyridine-2-carboxylic acid ethyl ester 
• 566198-39-8 5-(3-FORMYLPHENYL)PICOLINIC ACID 
• 566198-45-6 5-(2-FORMYLPHENYL)-PICOLINIC ACID 
• 845305-88-6 5-bromo-pyridine-2-carboxylic acid ethylamide 
• 364794-78-5 5-bromo-2-(1-piperidinylmethyl)pyridine 
• 1419603-15-8 methyl 2-(6-(4-fluorophenylcarbamoyl)pyridin-3-yl)propanoate 
• 1419603-17-0 2-(6-(4-fluorophenylcarbamoyl)pyridin-3-yl)propanoic acid 
• 1419598-71-2 5-(1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-N-(4-fluorophenyl)picolinamide 
• 29682-15-3 methyl 5-bromopicolinate 
• 1363374-48-4 C₁₇H₁₂N₂O₂ 
• 17880-61-4 methyl 5-ethynylpyridine-2-carboxylate 
• 1356633-38-9 5-bromo-N-(1-(4-cyanobenzyl)piperidin-4-yl)picolinamide 
• 1356625-87-0 N-(1-(4-cyanobenzyl)piperidin-4-yl)-5-(4-(4-cyanophenoxy)piperidin-1-yl)picolinamide 
• 88139-91-7 (5-bromopyridin-2-yl)methanol 

Relevant articles and documents

Fusaric acid and derivatives as novel antimicrobial agents

The synthesis and screening of several fusaric acid (FA) and analogues against five common clinical pathogens (gram-positive and gram-negative) and in vitro hemolytic activity assay in human red blood cells, for the first time, were reported. The biological results reveal that FA and its analogues exhibited moderate antimicrobial activities. Compounds 2–5 and 7 showed growth inhibitory activity in gram-positive bacteria. Compounds 6 and 9 showed growth inhibitory activity in both gram-positive and gram-negative bacteria. None of the compounds induce hemolysis, which is potent for future drug development on this template. In addition, the structure–activity relationship and docking studies are discussed.

Synthesis and SAR studies of novel 1,2,4-oxadiazole-sulfonamide based compounds as potential anticancer agents for colorectal cancer therapy

A diverse series of 1,2,4-oxadiazoles based substituted compounds were designed, synthesized and evaluated as anticancer agents targeting carbonic anhydrase IX (CAIX). Initial structure-activity analysis suggested that the thiazole/thiophene-sulfonamide conjugates of 1,2,4-oxadiazoles exhibited potent anticancer activities with low μM potencies. Compound OX12 exhibited antiproliferative activity (IC50 = 11.1 μM) along with appreciable inhibition potential for tumor-associated CAIX (IC50 = 4.23 μM) isoform. Therefore, OX12 was structurally optimized and its SAR oriented derivatives (OX17-27) were synthesized and evaluated. This iteration resulted in compound OX27 with an almost two-fold increase in antiproliferative effect (IC50 = 6.0 μM) comparable to the clinical drug doxorubicin and significantly higher potency against CAIX (IC50 = 0.74 μM). Additionally, OX27 treatment decreases the expression of CAIX, induces apoptosis and ROS production, inhibited colony formation and migration of colon cancer cells. Our studies provide preclinical rational for the further optimization of identified OX27 as a suitable lead for the possible treatment of CRC.

Fusaric acid and analogues as Gram-negative bacterial quorum sensing inhibitors

Taking advantage of microwave-assisted synthesis, efficient and expedite procedures for preparation of a library of fusaric acid and 39 analogues are reported. The fusaric acid analogues were tested in cell-based screening assays for inhibition of the las and rhl quorum sensing system in Pseudomonas aeruginosa and the lux quorum sensing system in Vibrio fischeri. Eight of the 40 compounds in the library including fusaric acid inhibited lux quorum sensing and one compound inhibited activity of the las quorum sensing system. To our delight, none of the compounds showed growth inhibitory effects in the tested concentration ranges.