[ CAS No. 1211534-25-6 ]

Name: 4-Bromo-5-chloro-2-methoxypyridine
Brand: Ambeed
SKU: A167184
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Quality Control of [ 1211534-25-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1211534-25-6 ]

SDS

Product Details of [ 1211534-25-6 ]

CAS No. :	1211534-25-6	MDL No. :	MFCD16609882
Formula :	C₆H₅BrClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	222.47	Pubchem ID :	70700260
Synonyms :

Computed Properties of [ 1211534-25-6 ]

TPSA :Topological Polar Surface Area	22.1	H-Bond Acceptor Count :	2
XLogP3 :	2.5	H-Bond Donor Count :	0
SP3 :	0.17	Rotatable Bond Count :	1

Safety of [ 1211534-25-6 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1211534-25-6 ]

Upstream synthesis route of [ 1211534-25-6 ]
Downstream synthetic route of [ 1211534-25-6 ]

[ 1211534-25-6 ] Synthesis Path-Upstream 1~4

1
[ 100367-39-3 ]
[ 1211534-25-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃;	To a solution of II (2.00 g, 10.6 mmol) in DMF (21 mL) was added NCS (2.98 g, 22.3 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was quenched with water, diluted with EtOAc, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried over MgS0₄, and concentrated. The crude product was purified by silica chromatography to provide 1J (2.15 g, 9.18 mmol, 86percent yield) as a white solid. LC-MS Anal. Calc'd for C₆H₅BrClNO: 220.92, found [M+H] 223.8. 1H NMR (400 MHz, CDC1₃) δ 8.15 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H).

Reference： [1] Patent: WO2015/171722, 2015, A1. Location in patent: Page/Page column 67; 68

2
[ 67-56-1 ]
[ 1187449-01-9 ]
[ 1211534-25-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: at 0 - 20℃; for 0.50 h; Stage #2: at 20 - 50℃; for 3.25 h;	[00253j 27B. 4-Bromo-5-chloro-2-methoxypyridine: To MeOH (390 mL) at 0 °C was added TMS-C1 (49.0 mL, 386 mmol). The reaction mixture was warmed to rt and stirred for 30 mm. To this solution was added 27A (20.0 g, 96.0 mmol). The reaction mixturewas stirred for 15 mill and then NaNO2 (2.74 g, 39.8 mmol) was added to the mixture at rt. The reaction mixture was stirred at 50 °C for 3 h. The reaction mixture was concentrated. The residue was diluted with EtOAc and then basified to pH = 11-13 with 1 N aq. NaOH and extracted with EtOAc (3x). The combined organic layers wereconcentrated. Purification by recrystallization from MeOH and water afforded 27B as white needles (18.0 g, 81.0 mmol, 84percent yield). LC-MS Anal. Calc’d for C6H5BrC1NO:220.92, found [M+H] 223.9.
84%	Stage #1: at 0 - 20℃; for 0.50 h; Stage #2: for 0.25 h; Stage #3: at 50℃; for 3.00 h;	81B. 4-Bromo-5-chloro-2-methoxypyridine To MeOH (390 mL) was added chlorotrimethylsilane (49 mL, 386 mmol) at 0° C., and the solution was warmed to rt and stirred for 30 min. To the resulting solution was added 4-bromo-5-chloropyridin-2-amine (20 g, 96 mmol), and the mixture was stirred for 15 min. To the reaction mixture was added sodium nitrite (2.7 g, 40 mmol) and the solution was stirred at 50° C. for 3 h. The reaction mixture was evaporated in vacuo, and the residue was diluted with EtOAc. The pH of the aqueous layer was adjusted to pH=˜12 via addition of 1 N NaOH, and the solution was extracted 3* with EtOAc. The combined organic layers were concentrated, and the residue was purified via recrystallization from MeOH and H₂O to give 4-bromo-5-chloro-2-methoxypyridine as white crystalline needles (18 g, 81 mmol, 84percent yield). LC-MS Anal. Calc'd for C₆H₅BrClNO 222.92. found [M+H] 223.9. ¹H NMR (400 MHz, CDCl₃) δ 8.18 (s, 1H), 7.08 (s, 1H), 3.94 (s, 4H).

Reference： [1] Patent: WO2014/78609, 2014, A1. Location in patent: Paragraph 00253
[2] Patent: US9133163, 2015, B2. Location in patent: Page/Page column 90

3
[ 84249-14-9 ]
[ 1211534-25-6 ]

Reference： [1] Patent: WO2014/78609, 2014, A1
[2] Patent: US9133163, 2015, B2

4
[ 128071-98-7 ]
[ 1211534-25-6 ]

Reference： [1] Patent: WO2015/171722, 2015, A1

[ 1211534-25-6 ] Synthesis Path-Downstream 1~10

1
[ 1211534-25-6 ]
N-(azetidin-3-yl)-2,4-dimethylquinoline-6-carboxamide [ No CAS ]
N-(1-(5-chloro-2-methoxypyridin-4-yl)azetidin-3-yl)-2,4-dimethylquinoline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 100℃;	N-(azetidin-3-yl)-2,4-dimethyl-quinoline-6-carboxamide (D) (15 mg, 0.060 mmol, 1.0 eq.), Pd2(dba)3 (5.4 mg, 0.010 mmol, 0.1 eq.), XantPhos (5.1 mg, 0.010 mmol, 0.009 eq.), Cs2C03 (40.45 mg, 0.12 mmol, 2.1 eq.), 4-bromo-5-chloro-2- methoxypyridine (15.68 mg, 0.070 mmol, 1.2 eq.) and 1,4-dioxane (0.294 mL) were charged into a reaction vial. After evacuated and purged with N2, the reaction vial was allowed to stir overnight at 100 °C. The reaction was then syringe filtered, diluted with DMSO and purified using reverse phase HPLC to afford the title compound (3.6 mg, 15 percent yield). NMR (400 MHz, DMSO-d6: delta 9.34 (d, J= 7.0 Hz, 1H), 8.65 (s, 1H), 8.22 (d, J= 8.8 Hz, 1H), 8.03 (d, J = 8.6 Hz, 1H), 7.90 (s, 1H), 7.42 (s, 1H), 5.93 (s, 1H), 4.92-4.89 (m, 1H), 4.60 (dd, J= 8.2, 8.2 Hz, 2H), 4.24 (dd, J= 7.5, 6.2 Hz, 2H), 3.84 (s, 3H), 2.78 (s, 3H), 2.69 (s, 3H); ES-MS [M+1]+: 397.3

Reference： [1]Patent: WO2018/112312,2018,A1.Location in patent: Paragraph 00225

2
[ 1211534-25-6 ]
1-(5-chloro-2-methoxy-4-pyridyl)azetidin-3-amine dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/112312,2018,A1

3
[ 1211534-25-6 ]
N-[1-(5-chloro-2-methoxy-4-pyridyl)azetidin-3-yl]-3,4-dimethylcinnoline-6-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/112312,2018,A1

4
[ 1211534-25-6 ]
2-((4S,5S)-1-(4-((1-(5-chloro-2-methoxypyridin-4-yl)piperidin-4-yl)oxy)phenyl)-4-methyl-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-yl)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 681 - 694

5
[ 1211534-25-6 ]
C₁₈H₂₁ClN₂O₄S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 681 - 694

6
[ 1211534-25-6 ]
C₂₅H₂₈ClF₃N₄O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 681 - 694

7
[ 1211534-25-6 ]
C₁₁H₂₄FNOSi [ No CAS ]
C₁₇H₂₈ClFN₂O₂Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 681 - 694

8
[ 1211534-25-6 ]
4-((3R,4R)-1-(5-chloro-2-methoxypyridin-4-yl)-3-methylpiperidin-4-yloxy)aniline [ No CAS ]

Reference： [1]Patent: WO2015/171722,2015,A1

9
[ 1211534-25-6 ]
5-chloro-2-methoxy-4-((3R,4R)-3-methyl-4-(4-nitrophenoxy)piperidin-1-yl)pyridine [ No CAS ]

Reference： [1]Patent: WO2015/171722,2015,A1

10
[ 1211534-25-6 ]
2-((2S,3S,4R)-1-(4-(((3R,4R)-1-(5-chloro-2-methoxypyridin-4-yl)-3-methylpiperidin-4-yl)oxy)phenyl)-4-(3-methoxypropoxy)-3-methylpyrrolidin-2-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2015/171722,2015,A1

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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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Code	Phrase
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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H319	Causes serious eye irritation
H320	Causes eye irritation
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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

[ CAS No. 1211534-25-6 ]

Quality Control of [ 1211534-25-6 ]

Related Doc. of [ 1211534-25-6 ]

Product Details of [ 1211534-25-6 ]

Computed Properties of [ 1211534-25-6 ]

Safety of [ 1211534-25-6 ]

Application In Synthesis of [ 1211534-25-6 ]

[ 1211534-25-6 ] Synthesis Path-Upstream 1~4

[ 1211534-25-6 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 1211534-25-6 ]

Chlorides

Bromides

Ethers

Related Parent Nucleus of [ 1211534-25-6 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 1211534-25-6 ]

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[ 1211534-25-6 ]