893440-50-1

Basic information

• Product Name: 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine
• Synonyms: 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine;5-Amino-6-methoxypyridine-3-boronic acid pinacol ester;2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine;2-Methoxy-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine;3-AMino-2-Methoxypyridine-5-boronic acid pinacol ester, 96%;2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine, 2-(5-Amino-6-methoxypyridin-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(Methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine;-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine
• CAS NO: 893440-50-1
• Molecular Formula: C₁₂H₁₉BN₂O₃
• Molecular Weight: 250.104
• Mol File: 893440-50-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 131-133℃
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine(893440-50-1)
• EPA Substance Registry System: 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine(893440-50-1)

Safety Data

• Hazardous Substances Data: 893440-50-1(Hazardous Substances Data)

Usage

Uses

It is used as a pharmaceutical intermediate.

Synthetic route

[2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]carbamic acid benzyl ester (893440-45-4) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
With hydrogen; palladium hydroxide on carbon In methanol at 20℃; for 5h;	97%

5-bromo-2-(methyloxy)-3-pyridinamine (884495-39-0) + bis(pinacol)diborane (73183-34-3) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 20 - 100℃;	95%
Stage #1: 5-bromo-2-(methyloxy)-3-pyridinamine; bis(pinacol)diborane In 1,4-dioxane for 0.166667h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	91.1%
With 3Na(1+)*C18H12O10PS3(3-); potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 80 - 90℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	86%

2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine (1083168-94-8) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
With hydrogen; Raney-Ni In methanol for 2h;	95%
With hydrogen In methanol for 2h;	95%
With hydrogen; Raney-Ni In methanol at 20℃; for 2h;	89%
With hydrogen In methanol at 20℃; for 2h;	89%
With palladium on activated charcoal In methanol at 20℃;

2-methoxy-3-amino-5-iodopyridine + bis(pinacol)diborane (73183-34-3) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 70 - 90℃; for 6h; Inert atmosphere;	84%

5-bromo-2-methoxy-3-nitropyridine (152684-30-5) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; iron / ethanol; water / 23 h / 10 - 25 °C / Industry scale; Inert atmosphere 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate / acetic anhydride / 3 h / Reflux 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 20 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 2 h / Reflux 2: hydrogen / methanol / 2 h / 20 °C View Scheme

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 2.75 h / 0 - 10 °C / Industry scale; Inert atmosphere 2: hydrogenchloride; iron / ethanol; water / 23 h / 10 - 25 °C / Industry scale; Inert atmosphere 3: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: methanol / 2.75 h / 0 - 10 °C / Inert atmosphere; Large scale 2: ethanol; iron / 20 - 25 °C / Large scale 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere View Scheme

bis(pinacol)diborane (73183-34-3) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 2 h / Reflux 2: hydrogen / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: palladium on activated charcoal / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / Reflux 2: hydrogen / Raney-Ni / methanol / 2 h / 20 °C View Scheme

2-methoxy-3-tert-butoxycarbonylamino-5-bromopyridine → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C / Industrial scale 2: potassium acetate; 3Na(1+)*C18H12O10PS3(3-); palladium diacetate / N,N-dimethyl-formamide / 20 h / 80 - 90 °C / Inert atmosphere View Scheme

5-bromo-2-methoxy-nicotinic acid (54916-66-4) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; diphenylphosphoranyl azide / 4 h / 10 - 80 °C / Industrial scale 2: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C / Industrial scale 3: potassium acetate; 3Na(1+)*C18H12O10PS3(3-); palladium diacetate / N,N-dimethyl-formamide / 20 h / 80 - 90 °C / Inert atmosphere View Scheme

2-methoxy-5-iodonicotinic acid → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; 3Na(1+)*C18H12O10PS3(3-) / 4 h / 10 - 80 °C 2: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C 3: potassium acetate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 70 - 90 °C / Inert atmosphere View Scheme

2-methoxynicotinic acid (16498-81-0) → 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / water / 16 h / 20 - 25 °C 2: triethylamine; diphenylphosphoranyl azide / 4 h / 10 - 80 °C / Industrial scale 3: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C / Industrial scale 4: potassium acetate; 3Na(1+)*C18H12O10PS3(3-); palladium diacetate / N,N-dimethyl-formamide / 20 h / 80 - 90 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: acetic acid; N-iodo-succinimide / 16 h / 35 °C 2: triethylamine; 3Na(1+)*C18H12O10PS3(3-) / 4 h / 10 - 80 °C 3: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C 4: potassium acetate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 70 - 90 °C / Inert atmosphere View Scheme

3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine (960613-96-1) + 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) → 5-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxypyridin-3-ylamine (1414463-76-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 0.5h;	98%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + [5-(6-bromoquinazolin-4-yl)pyridin-3-ylmethyl]carbamic acid tert-butyl ester (1414557-77-9) → {5-[6-(5-amino-6-methoxy-pyridin-3-yl)quinazolin-4-yl]pyridin-3-ylmethyl}carbamic acid tert-butyl ester (1414557-79-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 2h; Inert atmosphere; Reflux;	95%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + [3-(6-bromoquinazolin-4-yl)benzyl]carbamic acid tert-butyl ester (1414466-14-0) → {3-[6-(5-amino-6-methoxypyridin-3-yl)quinazolin-4-yl]benzyl}carbamic acid tert-butyl ester (1414466-20-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 1h;	94%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + {2-[4-(6-chloroimidazo[1,2-b]pyridazin-3-yl)pyrazol-1-yl]ethyl}carbamic acid tert-butyl ester (1414465-04-5) → 2-{4-[6-(5-Amino-6-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-3-yl]pyrazol-1-yl}(ethyl)carbamic acid tert-butyl ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 80℃; for 2h;	94%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + trifluoromethylsulfonic anhydride (358-23-6) → 1,1,1-trifluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methanesulfonamide (1366050-38-5)

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at -20℃; for 2h;	92%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 2-chloro-4-fluorobenzene-1-sulfonyl chloride (85958-57-2) → 2-chloro-4-fluoro-N-[2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzene-1-sulfonamid

Conditions	Yield
With pyridine at 28℃; for 18h;	90.5%
With pyridine at 25℃; for 16h;

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 7-bromo-3-(2-(dimethylamino)ethoxy)-4H-pyrido[1,2-a]pyrimidin-4-one → 7-(5-amino-6-methoxypyrimidin-3-yl)-3-(2-(dimethylamino)ethoxy)-pyrido[1,2-a]pyrimidin-4-one

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 95℃; Inert atmosphere;	84.24%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (1246372-52-0) → 5-(5-iodoimidazo[2,1-b][1,3,4]thiadiazol-2-yl)-2-methoxypyridin-3-ylamine (1246373-15-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 110℃;	84%
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water at 110℃; for 2.5h;	23%
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water for 2h; Inert atmosphere; Reflux;
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 2h; Suzuki Coupling; Inert atmosphere; Reflux;

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + [1-(6-bromoquinazolin-4-yl)piperidin-4-ylmethyl]carbamic acid tert-butyl ester (1426662-98-7) → {1-[6-(5-amino-6-methoxypyridin-3-yl)quinazolin-4-yl]piperidin-4-ylmethyl}carbamic acid tert-butyl ester (1414458-32-4)

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 120℃; Inert atmosphere;	84%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; Inert atmosphere;	33%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 3-Carboxybenzenesulfonyl chloride (4025-64-3) → C19H23BN2O7S (1414456-20-4)

Conditions	Yield
With pyridine at 0℃; for 3h;	82%

6-bromo-4-chloroquinoline (65340-70-7) + 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) → 5-(4-chloro-quinolin-6-yl)-2-methoxy-pyridin-3-ylamine (1414456-84-0)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 1h;	81%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 100℃; for 1h; Sealed tube;	73%

2,6-Dichloropyrimidine (3934-20-1) + 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) → 2-methoxy-3-amino-5-((2-chloro)pyrimidin-4-yl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 2h; Inert atmosphere;	73%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + (4-bromobenzyl)dimethylamine (6274-57-3) → 5-(4-((dimethylamino)methyl)phenyl)-2-methoxypyridin-3-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 2h; Inert atmosphere; Reflux;	71.4%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + methanesulfonyl chloride (124-63-0) → N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methanesulfonamide (1083326-75-3)

Conditions	Yield
With pyridine at 20℃; for 18h;	70%
With pyridine at 20℃; for 18h;
With pyridine at 20℃; for 18h;

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + [5-(6-chloroimidazo[1,2-b]pyridazin-3-yl)pyridin-3-ylmethyl]carbamic acid tert-butyl ester (1414457-07-0) → {5-[6-(5-amino-6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-3-yl]pyridin-3-ylmethyl}carbamic acid tert-butyl ester (1414464-56-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 80℃; for 2h;	67%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 4-chloro-6-iodo-thieno[2,3-d]pyrimidine (552295-08-6) → 5-(4-chlorothieno[2,3-d]pyrimidin-6-yl)-2-methoxypyridin-3-ylamine (1414465-90-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 100℃; for 1h;	67%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + N-(3-bromo-2-methylphenyl)-4-(tert-butyl)benzamide (1013116-83-0) → N-(3-(5-amino-6-methoxypyridin-3-yl)-2-methylphenyl)-4-tert-butylbenzamide (1013116-81-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; for 16h;	64%

3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine (960613-96-1) + 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + (3-{[(tert-butoxycarbonyl)amino]methyl}phenyl)boronic acid (199609-62-6) → {3-[5-(5-amino-6-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzyl}carbamic acid tert-butyl ester (1414463-32-3)

Conditions

Yield

Stage #1: 3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine; 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water at 80℃; for 0.5h; Stage #2: (3-{[(tert-butoxycarbonyl)amino]methyl}phenyl)boronic acid With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 5h;

63%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 2,4-difluorobenzene-1-sulfonyl chloride (13918-92-8) → N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide (1083326-73-1)

Conditions	Yield
With pyridine at 20℃;	59%
In pyridine at 20℃;	59%
With pyridine at 20℃; for 2h;
With pyridine at 20℃; Inert atmosphere;
With pyridine at 20℃; for 2h;

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 3-bromo-6-iodoimidazo[1,2-a]pyridine (1146615-52-2) → 5-(3-bromoimidazo[1,2-a]pyridin-6-yl)-2-methoxypyridin-3-ylamine (1414472-94-8)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water at 110℃; for 0.666667h; Microwave irradiation;	57%

3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine (960613-96-1) + 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + [5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester (1257554-93-0) → C22H23N7O3

Conditions

Yield

Stage #1: 3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine; 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In dichloromethane at 80℃; for 0.5h; sealed tube; Stage #2: [5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester; bis-triphenylphosphine-palladium(II) chloride In dichloromethane at 80℃; for 22h;

56%

3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine (960613-96-1) + 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + [5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester (1257554-93-0) → {5-[5-(5-amino-6-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl]pyridin-3-ylmethyl}carbamic acid tert-butyl ester

Conditions

Yield

Stage #1: 3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine; 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane at 80℃; for 0.5h; Stage #2: [5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester With bis-triphenylphosphine-palladium(II) chloride at 80℃; for 22h;

56%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + trifluoromethanesulfonic acid 8-chloro-[1,5]naphthyridin-2-yl ester (1092565-20-2) → 5-(8-chloro-[1,5]naphthyridin-2-yl)-2-methoxy-pyridin-3-ylamine (1414473-21-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 0.5h;	55%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + p-tert-butyl benzoyl chloride (1710-98-1) → 4-tert-butyl-N-[2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.166667h;	52%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 7-bromo-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine → 7-(5-amino-6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 85℃; for 2.5h;	52%

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (893440-50-1) + 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (1450642-74-6) → 5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-amine (1534379-11-7)

Conditions	Yield
Stage #1: 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine; 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine In 1,2-dimethoxyethane; water for 0.166667h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 2.41667h; Inert atmosphere;	49.2%

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 54916-66-4 5-bromo-2-methoxy-nicotinic acid 
• 1407521-93-0 2-methoxy-5-iodonicotinic acid 
• 16498-81-0 2-methoxynicotinic acid 
• 1083168-94-8 2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine 
• 67443-38-3 5-bromo-2-chloro-3-nitropyridine 
• 152684-30-5 5-bromo-2-methoxy-3-nitropyridine 
• 884495-39-0 5-bromo-2-(methyloxy)-3-pyridinamine 
• 893440-45-4 [2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]carbamic acid benzyl ester 

Downstream Products

• 1083326-75-3 N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methanesulfonamide 
• 1198803-04-1 N-{6-[5-amino-6-(methyloxy)-3-pyridinyl]-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide 
• 1361970-55-9 N-[5-[4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide 
• 1361970-34-4 N-[5-[4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-oxazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide tosylate salt 
• 1361970-37-7 N-[5-[4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-oxazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide mesitylenesulfonate salt 
• 1366049-56-0 2,4-difluoro-N-(2-methoxy-5-(1-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)pyridin-3-yl)benzenesulfonamide 
• 1366050-21-6 N-(2-methoxy-5-(1-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)pyridin-3-yl)-4-methylbenzenesulfonamide 
• 1414456-20-4 C₁₉H₂₃BN₂O₇S 
• 1425335-63-2 N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide 
• 1414463-32-3 {3-[5-(5-amino-6-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzyl}carbamic acid tert-butyl ester 
• 1414466-20-8 {3-[6-(5-amino-6-methoxypyridin-3-yl)quinazolin-4-yl]benzyl}carbamic acid tert-butyl ester 

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