1072448-08-8|Methyl 3-amino-5-bromopicolinate| Ambeed

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Quality Control of [ 1072448-08-8 ] Purity: 98% SDS Specification

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Product Details of [ 1072448-08-8 ]

CAS No. :	1072448-08-8
Formula :	C₇H₇BrN₂O₂
M.W :	231.05
SMILES Code :	O=C(C1=NC=C(Br)C=C1N)OC
MDL No. :	MFCD17015929
InChI Key :	DWRSWUPHDNTLKJ-UHFFFAOYSA-N
Pubchem ID :	50989141

Safety of [ 1072448-08-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1072448-08-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1072448-08-8 ]

[ 1072448-08-8 ] Synthesis Path-Downstream 1~27

1
[ 1072448-08-8 ]
C₇H₆ClFZn*ClLi [ No CAS ]
[ 863443-05-4 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 8422 - 8436.

2
[ 1072448-08-8 ]
[ 627-41-8 ]
[ 1425842-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) chloride; In tetrahydrofuran; at 80.0℃; for 5.0h;Inert atmosphere;	a) 3-Amino-5-(3-methoxy-prop-1 -ynyl)-pyridine-2-carboxylic acid methyl ester To a solution of 3-methoxy-propyne (421 mg, 6 mmol), bis(triphenylphosphine)palladium(ll) chloride (84 mg, 0.12 mmol), copper(l) iodide (23 mg, 0.12 mmol) and NEt3 (1.17 ml, 8.4 mmol) in THF (10 ml) under Argon was added <strong>[1072448-08-8]3-amino-5-bromo-pyridine-2-carboxylic acid methyl ester</strong> (277 mg, 1.2 mmol) and the mixture was heated to 80 C for 5 h. At 0 C water (12 ml) was added and the mixture was extracted with EtOAc, the combined organic layers were washed with half-saturated aq. sodium chloride, dried with Na2S04 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1 :4) to provide the title compound as orange solid. HPLC: RtHi = 0.67 min; ESIMS [M+H]+ = 221.1 ; 1H-NMR (600 MHz, DMSO-c 6): delta 7.85 (d, 1 H), 7.33 - 7.22 (m, 1 H), 6.77 (s, 2H), 4.35 (s, 2H), 3.80 (s, 3H), 3.33 (s, 3H).

References: [1]Patent: WO2013/27188,2013,A1 .Location in patent: Page/Page column 95.

3
[ 1072448-08-8 ]
[ 1425842-49-4 ]

References: [1]Patent: WO2013/27188,2013,A1 .

4
[ 870997-85-6 ]
[ 74-88-4 ]
[ 1072448-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl acetamide; at 20.0℃;	Intermediate 13: 3-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester: [00293] 3-Amino-5-b mmol) was mixed with K2CO3 (1.38 g, 10 mmol) and CH3I (CAS: 74-88-4, 620 muL, 10 mmol) in DMA (40 mL). The resulting mixture was stirred at ambient temperature overnight. Next, the mixture was diluted with water which gives rise to a suspension. Filtration, followed by washing with water and subsequent drying yielded the titled compound that was used as such.

References: [1]Patent: WO2016/193812,2016,A1 .Location in patent: Paragraph 00293.

5
[ 1072448-08-8 ]
3-(2-fluoro-4-trifluoromethoxyphenylsulfanyl)propionic acid 2-ethylhexyl ester [ No CAS ]
3-amino-5-(2-fluoro-4-trifluoromethoxyphenylsulfanyl)pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis(diisopropylphosphino)ferrocene; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 105.0℃;Inert atmosphere;	Step 2: 3-Amino-5-(2-fluoro-4-trifluoromethoxy-phenylsulfanyl)-pyridine-2-carboxylic acid methyl ester: [00278] 3-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester (Int 13, 3.45 g, 14.9 mmol) was mixed with 3-(2-fluoro-4-trifluoromethoxy-phenylsulfanyl)-propionic acid 2-ethyl-hexyl 103 ABV12212USO1 ester (5.91 g, 14.9 mmol), DBU (4.46 mL, 29.9 mmol), Pd(OAc)2 (168 mg, 0.75 mmol) and DiPPF (624 mg, 0.149 mmol) in dioxane (75 mL). The mixture was degassed and put under a N2 atmosphere. The mixture was then heated at 105 C overnight after which it was diluted with EtOAc and extracted with water. The organic phase was separated, dried and concentrated. Next, the residue was purified by chromatography (a gradient from 100% petroleum ether to 20% EtOAc in petroleum ether was applied) to give the titled compound.

References: [1]Patent: WO2016/193812,2016,A1 .Location in patent: Paragraph 00278.

6
[ 1072448-08-8 ]
3-(2-fluoro-4-trifluoromethylphenylsulfanyl)propionic acid 2-ethylhexyl ester [ No CAS ]
3-amino-5-(2-fluoro-4-trifluoromethylphenylsulfanyl)pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis(diisopropylphosphino)ferrocene; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 105.0℃;Inert atmosphere;	Step 2: 3-Amino-5-(2-fluoro-4-trifluoromethyl-phenylsulfanyl)-pyridine-2-carboxylic acid methyl ester: [00282] 3-(2-Fluoro-4-trifluoromethyl-phenylsulfanyl)-propionic acid 2-ethyl-hexyl ester (5.67 g, 14.9 mmol) was mixed with <strong>[1072448-08-8]3-amino-5-bromo-pyridine-2-carboxylic acid methyl ester</strong> (Int 13, 3.45 g, 14.9 mmol), Pd(OAc)2 (168 mg, 0.75 mmol), DiPPF (624 mg, 0.15 mmol) and DBU (4.46 mL, 29.9 mmol) in dioxane (75 mL). The mixture was degassed and put under a N2 atmosphere. The mixture was then heated at 105 C overnight after which it was diluted with EtOAc and extracted with water. The organic phase was separated, dried and concentrated. Next, the residue was purified by chromatography (a gradient from 100% petroleum ether to 20% EtOAc in petroleum ether was applied) to give the titled compound.

References: [1]Patent: WO2016/193812,2016,A1 .Location in patent: Paragraph 00282.

7
[ 1072448-08-8 ]
3-amino-5-(2-fluoro-4-trifluoromethoxybenzenesulfonyl)pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

8
[ 1072448-08-8 ]
(3-amino-5-[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

9
[ 1072448-08-8 ]
3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

10
[ 1072448-08-8 ]
3-amino-5-(2-fluoro-4-trifluoromethoxyphenylsulfanyl)pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

11
[ 1072448-08-8 ]
3-amino-5-(2-fluoro-4-trifluoromethylbenzenesulfonyl)pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

12
[ 1072448-08-8 ]
3-amino-5-(2-fluoro-4-trifluoromethylphenylsulfanyl)pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

13
[ 1072448-08-8 ]
3-amino-N-(3-tert-butoxy-2-hydroxypropyl)-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

14
[ 1072448-08-8 ]
3-amino-N-[(2S)-2-hydroxypropyl]-5-[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

15
[ 1072448-08-8 ]
3-amino-5-[(4-fluorobenzyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

16
[ 1072448-08-8 ]
3-amino-5-[2-(hydroxymethyl)pyrrolidin-1-yl]sulfonyl}-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

17
[ 1072448-08-8 ]
3-amino-5-[(4-fluorobenzyl)(methyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

18
[ 1072448-08-8 ]
3-amino-N-[(2S)-2-hydroxypropyl]-5-[(2-methoxyethyl)(methyl)sulfamoyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

19
[ 1072448-08-8 ]
3-amino-5-[cyclobutyl(methyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

20
[ 1072448-08-8 ]
C₉H₁₂ClN₃O₄S [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

21
[ 1072448-08-8 ]
[ 100-53-8 ]
3-amino-5-(benzylsulfanyl)-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2016/193812,2016,A1 .

22
[ 1072448-08-8 ]
[ 100-53-8 ]
methyl 3-amino-5-(benzylsulfanyl)pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
518 mg	With 4-methyl-morpholine; 1,8-diazabicyclo[5.4.0]undec-7-ene; for 0.666667h;Inert atmosphere; Reflux;	Step 3: methyl 3-amino-5-(benzylsulfanyl)pyridine-2-carboxylate: [00313] A flask containing <strong>[1072448-08-8]methyl 3-amino-5-bromopyridine-2-carboxylate</strong> (826 mg, 3.57 mmol, Step 2), benzylthiol (630 muL, 5.37 mmol) and DBU (1.6 mL, 10.7 mmol) mixed with N- methylmorpholine (8 mL) was flushed with nitrogen, and the reaction mixture heated at reflux for 40 minutes, with brisk stirring as a second phase forms, then brought to room temperature. The mixture was partially concentrated, treated with 1 M aqueous citric acid (7 mL) and extracted four times with 1:1 CH2Cl2/heptane. The combined organic phases were washed with 1:11 M aqueous citric acid/brine, and the separated aqueous phase was extracted once with 1:1 CH2Cl2/heptane. The organic phases were dried (Na2SO4), combined and filtered with a thorough CH2Cl2 rinse of the solids. The filtrate was concentrated and chromatographed on silica (0 to 10% ethyl acetate in 1:1 CH2Cl2/heptanes) to give the titled compound (518 mg). 1H NMR (500 MHz, DMSO-d6) delta ppm 3.77 (s, 3H), 4.30 (s, 2H), 6.70 (s, 2H), 7.14 (d, J = 2.0 Hz, 1H), 7.24 - 7.28 (m, 1H), 7.31 - 7.35 (m, 2H), 7.40 - 7.43 (m, 2H), 7.73 (d, J = 2.0 Hz, 1H); MS (DCI) m/z 275 (M+H)+.

References: [1]Patent: WO2016/193812,2016,A1 .Location in patent: Paragraph 00313.

23
methyl 5-bromo-3-[(4-methoxyphenyl)methylamino]pyridine-2-carboxylate [ No CAS ]
[ 1072448-08-8 ]

Yield	Reaction Conditions	Operation in experiment
905 mg	With trifluoroacetic acid; In dichloromethane; at 40.0℃; for 18.0h;	Step 2: methyl 3-amino-5-bromopyridine-2-carboxylate: [00312] Methyl 5-bromo-3-[(4-methoxybenzyl)amino]pyridine-2-carboxylate (1.36 g, <3.8 mmol, Step 1) was dissolved into anhydrous CH2Cl2 (6 mL) and trifluoroacetic acid (2 mL) and heated at 40 C for 18 hours. The reaction mixture was concentrated, diluted with CH2Cl2/heptane, filtered through silica with 1:1 ethyl acetate/heptane, and concentrated. The residue was chromatographed on silica (5 to 15% ethyl acetate in 1:1 CH2Cl2/heptane) to give the titled compound (905 mg). 1H NMR (400 MHz, CDCl3) delta ppm 3.95 (s, 3H), 6.90 (br s, 2H), 7.34 (d, J = 1.9 Hz, 1H), 8.11 (d, J = 1.9 Hz, 1H); MS (ESI) m/z 231 / 233 (M+H)+.

References: [1]Patent: WO2016/193812,2016,A1 .Location in patent: Paragraph 00312.

24
[ 1211538-72-5 ]
[ 1072448-08-8 ]

References: [1]Patent: WO2016/193812,2016,A1 .

25
[ 1072448-08-8 ]
N-[5-cyano-2-(hydroxymethyl)pyridin-3-yl]-2,2-dimethylpropanamide [ No CAS ]

References: [1]Patent: WO2018/167001,2018,A1 .

26
[ 1072448-08-8 ]
methyl 5-cyano-3-(2,2-dimethylpropanoylamino)pyridine-2-carboxylate [ No CAS ]

References: [1]Patent: WO2018/167001,2018,A1 .

27
[ 1072448-08-8 ]
[ 3282-30-2 ]
methyl 5 -bromo-3-(2,2-dimethylpropanoylamino)pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; at 20.0℃; for 18.0h;	To a light yellow suspension of <strong>[1072448-08-8]methyl 3-amino-5-bromopyridine-2-carboxylate</strong> (CAS-RN 1072448-08-8; 900 mg, 3.7 mmol) in pyridine (15 mL) was added 2,2-dimethylpropanoyl chloride (CAS-RN 3282-30-2; 546 mg, 4.44 mmol). The colour turned to light red. More 2,2- dimethylpropanoyl chloride (1.092g, 8.88 mmol) was added and the reaction was stuffed at roomtemperature for 18 h, then partitioned between ice and 1 M aq. hydrochloric acid solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated. Chromatography (silica gel, gradient dichloromethane / heptane 1: 1 to dichloromethane) produced the title compound (385 mg, 99 %). White solid, MS: 317.0 (M+H).

References: [1]Patent: WO2018/167001,2018,A1 .Location in patent: Page/Page column 83.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

Related Functional Groups of
[ 1072448-08-8 ]

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[ 1072448-08-8 ]

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P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1072448-08-8

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