[ CAS No. 1254473-68-1 ]

Name: 1254473-68-1|(R)-1-(3,5-Dichloropyridin-4-yl)ethanol|98%
Brand: Ambeed
SKU: A470505
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Quality Control of [ 1254473-68-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1254473-68-1 ]

CAS No. :	1254473-68-1	MDL No. :	MFCD22665798
Formula :	C₇H₇Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KCPDCYCCMCEYQN-SCSAIBSYSA-N
M.W :	192.04	Pubchem ID :	78357890
Synonyms :

Safety of [ 1254473-68-1 ]

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

Application In Synthesis of [ 1254473-68-1 ]

* 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 [ 1254473-68-1 ]

[ 1254473-68-1 ] Synthesis Path-Downstream 1~48

1
[ 1370347-50-4 ]
(R)-1-(3,5-dichloropyridin-4-yl)ethan-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6690 - 6708

2
[ CAS Unavailable ]
[ 1254473-68-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide / water; ethanol / 2 h / 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 3: sodium hydroxide / water; ethanol / 20 °C

3
C₁₆H₁₃Cl₄NO₃ [ No CAS ]
[ 1370347-50-4 ]
(R)-1-(3,5-dichloropyridin-4-yl)ethan-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6690 - 6708

4
[ 1989596-75-9 ]
[ 1254473-68-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide / water; ethanol / 2 h / 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 3: sodium hydroxide / water; ethanol / 20 °C

5
[ CAS Unavailable ]
[ 1254473-68-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water at 20℃;

6
[ 1254473-66-9 ]
(R)-1-(3,5-dichloropyridin-4-yl)ethan-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6690 - 6708
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 6690 - 6708
[3]Patent: CN103819396,2016,B

7
[ 2457-47-8 ]
[ 1254473-68-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / -78 °C 2: dmap; dicyclohexyl-carbodiimide / toluene / 0 °C 3: sodium hydroxide / water; ethanol / 2 h / 20 °C 4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 5: sodium hydroxide / water; ethanol / 20 °C
	Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / -78 °C 2: dmap; dicyclohexyl-carbodiimide / toluene / 0 °C 3: sodium hydroxide / water; ethanol / 2 h / 20 °C 4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 5: sodium hydroxide / water; ethanol / 20 °C
	Multi-step reaction with 3 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran / 3 h / -78 °C 2: pyridinium chlorochromate / dichloromethane / 10 h / 20 °C 3: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / dichloromethane / 12 h / -10 °C

Reference： [1]Yan, Wei; Wang, Xinyi; Dai, Yang; Zhao, Bin; Yang, Xinying; Fan, Jun; Gao, Yinglei; Meng, Fanwang; Wang, Yuming; Luo, Cheng; Ai, Jing; Geng, Meiyu; Duan, Wenhu [Journal of Medicinal Chemistry, 2016, vol. 59, # 14, p. 6690 - 6708]
[2]Yan, Wei; Wang, Xinyi; Dai, Yang; Zhao, Bin; Yang, Xinying; Fan, Jun; Gao, Yinglei; Meng, Fanwang; Wang, Yuming; Luo, Cheng; Ai, Jing; Geng, Meiyu; Duan, Wenhu [Journal of Medicinal Chemistry, 2016, vol. 59, # 14, p. 6690 - 6708]
[3]Current Patent Assignee: SICHUAN UNIVERSITY - CN103819396, 2016, B

8
[ 1254473-68-1 ]
[ 124-63-0 ]
[ 1254473-70-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine In dichloromethane Cooling with ice;	4 (R) -1- (3,5-dichloropyridin-4-yl) ethyl methanesulfonate (V) A solution of (R) -1- (3,5-dichloropyridin-4-yl) ethanol (IV) (4.5 g, 23.43 mmol) and triethylamine (8.54 g, 84.35 mmol) in anhydrous dichloromethane 100 ml), and methanesulfonyl chloride (3.22 g, 28.12 mmol) was added dropwise under ice-cooling.The reaction solution was poured into saturated sodium bicarbonate solution, the organic layer was separated, and the organic layer was washed with methylene chloride, and the organic layer was combined and the organic layer was washed with saturated brine. The organic layer was washed three times with the organic layer and the organic layer After drying over anhydrous sodium sulfate, the dichloromethane was distilled off under reduced pressure and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 20: 1) to give 5.78 g of pure white crystals in 91% yield.
	With triethylamine In dichloromethane at 20℃; for 1h;	6 Synthesis Intermediate 6-1: 5-((R)-1-(3,5-Dichloropyridin-4-yl)ethoxy)-1-(tetrahydro-2H-pyran-2-yl)- 1H-indazole-3-carbaldehyde (S)-1-(3,5-Dichloropyridin-4-yl)ethan-1-ol (200.0mg, 1.05mmol) and triethylamine (317.6mg, 3.14mmol) were dissolved in 20ml DCM, 0 Methanesulfonyl chloride (131.9 mg, 1.15 mmol) was added dropwise to the reaction solution, and reacted at room temperature for 1 hour. The reaction solution was quenched by adding water, extracted with dichloromethane twice, and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. Dissolve 1-4 (270.0mg, 1.09mmol) and the concentrate in 20ml DMF, add cesium carbonate (684.2mg, 2.10mmol), and react at 60°C for 16 hours. Water was added to the reaction solution, extracted twice with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column to obtain 289.3 mg of Intermediate 6-1 with a yield of 65.5%.
	With triethylamine In dichloromethane at 0℃; for 0.5h;

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN103819396, 2016, B Location in patent: Paragraph 0029-0031
[2]Current Patent Assignee: HENAN MEDINNO PHARMACEUTICAL TECH; HENAN MAIYINGNUO PHARMACEUTICAL TECH - CN113666911, 2021, A Location in patent: Paragraph 0304; 0307; 0309-0311
[3]Shao, Min; Chen, Xiaojuan; Yang, Fang; Song, Xiaojuan; Zhou, Yang; Lin, Qianmeng; Fu, Ying; Ortega, Raquel; Lin, Xiaojing; Tu, Zhengchao; Patterson, Adam V.; Smaill, Jeff B.; Chen, Yongheng; Lu, Xiaoyun [Journal of Medicinal Chemistry, 2022, vol. 65, # 6, p. 5113 - 5133]

9
[ 402561-66-4 ]
[ 1254473-68-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane at -10℃; for 12h;	3 (R)-1-(3,5-dichloropyridin-4-yl)ethanol (IV) A solution of (S) -2-methyl-CBS-oxazaborolidine (1 M in toluene, 5.3 ml, 5.26 mmol) and borane dimethyl sulfide complex (BH3-dMS, 10M dimethyl sulfide solution, 13.2 ml, 131.5 mmol) was dissolved in anhydrous dichloromethane (DCM, 100 ml),stirred at10°C for 10 min, and 3,5-dichloro-4- Acetylpyridine (III) (5 g, 26.3 mmol) in DCM (30 ml) was added dropwise to 10oC for 12 h, slowly warmed to room temperature and slowly dripped into the methanol quenching reaction.Drop finished, 70oC reflow 3h.The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 20: 1) to give 4.87 g of a colorless oil; 96% yield and 98.14% ee

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN103819396, 2016, B Location in patent: Paragraph 0026-0028

10
[ 1254473-68-1 ]
[ 2745123-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 1 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C 3.1: potassium permanganate; water / acetonitrile / 16 h / 20 °C 4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C 4.2: 2 h / 50 °C