[ CAS No. 110860-92-9 ] {[proInfo.proName]}

Name: 110860-92-9|5,6-Dichloropyridin-3-ol|98%
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SKU: A117492
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Quality Control of [ 110860-92-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 110860-92-9 ]

Product Details of [ 110860-92-9 ]

CAS No. :	110860-92-9	MDL No. :	MFCD09835219
Formula :	C₅H₃Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GMHPKIGFTDRQBP-UHFFFAOYSA-N
M.W :	163.99	Pubchem ID :	14391672
Synonyms :

Calculated chemistry of [ 110860-92-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.28
TPSA :	33.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	2.09
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	2.23
Consensus Log Po/w :	1.78

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.69
Solubility :	0.333 mg/ml ; 0.00203 mol/l
Class :	Soluble
Log S (Ali) :	-2.46
Solubility :	0.573 mg/ml ; 0.00349 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.67
Solubility :	0.348 mg/ml ; 0.00212 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 110860-92-9 ]

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

Application In Synthesis of [ 110860-92-9 ]

* 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.

Upstream synthesis route of [ 110860-92-9 ]
Downstream synthetic route of [ 110860-92-9 ]

[ 110860-92-9 ] Synthesis Path-Upstream 1~6

1
[ 110861-18-2 ]
[ 110860-92-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2 h;	A solution of KOH (728 mg, 13 mmol) in 7 ml of water was added to a solution of compound 3 (1 g, 4.8 mmol) in 10 ml of THF at 0 °C. After addition, the mixture was stirred at ambient temperature for 2 h. Then the mixture added dilute hydrochloric acid to adjust the pH value to weak alkaline and filtered. The filter residue was purified by recrystallization to give compound 4(517 mg, y: 65percent). H NMR (400 MHz, DMSO-d6) 5(ppm): 7.47(d, 1 H), 7.93(d, 1 H), 10.72(s, 1 H).
4.8 g	With potassium hydroxide In water at 0℃;	Acetic acid 5,6-dichloro-pyridin-3-yl ester (7.00 g, 34.0 mmol, 1.0 equiv.) was added to KOH (5.70 g) in H₂O (50.0 mL) at 0 °C. The mixture was stirred overnight. The solution was made acidic (pH 5) by addition of glacial acetic acid and 5,6-dichloro-pyridin-3-ol (4.80 g, 29.0 mmol) precipitated, and was filtered off as a white solid.

Reference： [1] Synthesis, 1990, # 6, p. 499 - 501
[2] Patent: WO2016/91731, 2016, A1, . Location in patent: Page/Page column 140
[3] Patent: US6432880, 2002, B1,
[4] Patent: US6133253, 2000, A,
[5] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2303 - 2307

2
[ 98121-41-6 ]
[ 110860-92-9 ]

Reference： [1] Synthesis, 1990, # 6, p. 499 - 501
[2] Patent: US4756739, 1988, A,
[3] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2303 - 2307
[4] Patent: WO2016/91731, 2016, A1,

3
[ 22353-40-8 ]
[ 110860-92-9 ]

Reference： [1] Synthesis, 1990, # 6, p. 499 - 501
[2] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2303 - 2307

4
[ 5418-51-9 ]
[ 110860-92-9 ]

Reference： [1] Synthesis, 1990, # 6, p. 499 - 501

5
[ 22353-38-4 ]
[ 110860-92-9 ]

Reference： [1] Synthesis, 1990, # 6, p. 499 - 501

6
[ 74115-12-1 ]
[ 53335-73-2 ]
[ 24525-62-0 ]
[ 110860-92-9 ]

Reference： [1] Synthesis, 1990, # 6, p. 499 - 501
[2] Synthesis, 1990, # 6, p. 499 - 501

[ 110860-92-9 ] Synthesis Path-Downstream 1~72

1
[ 74115-12-1 ]
[ 53335-73-2 ]
[ 24525-62-0 ]
[ 110860-92-9 ]

Reference： [1]Synthesis,1990,p. 499 - 501
[2]Synthesis,1990,p. 499 - 501

2
[ 116-15-4 ]
[ 110860-92-9 ]
[ 110860-98-5 ]

Reference： [1]Synthesis,1990,p. 604 - 608

3
[ 75-45-6 ]
[ 110860-92-9 ]
[ 110860-85-0 ]

Reference： [1]Synthesis,1990,p. 604 - 608

4
[ 116-14-3 ]
[ 110860-92-9 ]
[ 110861-09-1 ]

Reference： [1]Synthesis,1990,p. 604 - 608

5
[ 79-38-9 ]
[ 110860-92-9 ]
[ 110860-83-8 ]

Reference： [1]Synthesis,1990,p. 604 - 608

6
[ 1623-05-8 ]
[ 110860-92-9 ]
[ 130115-92-3 ]

Reference： [1]Synthesis,1990,p. 604 - 608

7
[ 110861-18-2 ]
[ 110860-92-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide; In tetrahydrofuran; water; at 0 - 20℃; for 2.0h;	A solution of KOH (728 mg, 13 mmol) in 7 ml of water was added to a solution of compound 3 (1 g, 4.8 mmol) in 10 ml of THF at 0 C. After addition, the mixture was stirred at ambient temperature for 2 h. Then the mixture added dilute hydrochloric acid to adjust the pH value to weak alkaline and filtered. The filter residue was purified by recrystallization to give compound 4(517 mg, y: 65%). H NMR (400 MHz, DMSO-d6) 5(ppm): 7.47(d, 1 H), 7.93(d, 1 H), 10.72(s, 1 H).
	With sodium hydroxide; acetic acid; In ice-water; water; ethyl acetate;	Intermediate 1.6: 2,3-Dichloro-5-hydroxypyridine At 0 C., a solution of 13 g of sodium hydroxide in 80 ml of water was added to 16 g of 5-acetyloxy-2,3-dichloropyridine in 100 ml of ice-water. The mixture was subsequently initially stirred at 0 C. for one hour and then at approximately 20 C. for 17 hours, and the reaction mixture was then washed with 150 ml of ethyl acetate. The mixture was acidified up to a pH of 4-5 by addition of acetic acid and then extracted three times with 100 ml of ethyl acetate each time. The combined organic phases were dried over magnesium sulfate and finally concentrated. Yield: 12.2 g.
4.8 g	With potassium hydroxide; In water; at 0℃;	Acetic acid 5,6-dichloro-pyridin-3-yl ester (7.00 g, 34.0 mmol, 1.0 equiv.) was added to KOH (5.70 g) in H2O (50.0 mL) at 0 C. The mixture was stirred overnight. The solution was made acidic (pH 5) by addition of glacial acetic acid and 5,6-dichloro-pyridin-3-ol (4.80 g, 29.0 mmol) precipitated, and was filtered off as a white solid.

5.4 g (94%)

With potassium hydroxide; acetic acid;

15d. 5,6-dichloro-3-pyridinol The product of Example 15c (9.15 g, 44.4 mmol) was treated with 2 N potassium hydroxide solution (67 mL, 133 mmol), and the mixture was stirred for 18 hours. The mixture was diluted with H2 O and treated with acetic acid to pH 6-7. The solid precipate was collected by filtration and washed with H2 O, then dried at 50 C. to afford 5.4 g (94%) of the title compound as a white solid: MS (CI/NH3) 164, 166, 168 (M+H+).

Reference： [1]Synthesis,1990,p. 499 - 501
[2]Patent: WO2016/91731,2016,A1 .Location in patent: Page/Page column 140
[3]Patent: US6432880,2002,B1
[4]Tetrahedron Letters,2013,vol. 54,p. 2303 - 2307
[5]Patent: US6133253,2000,A

8
[ 84145-18-6 ]
[ 110860-92-9 ]
[ 130115-91-2 ]

Reference： [1]Synthesis,1990,p. 604 - 608

9
[ 110860-92-9 ]
[ 110860-93-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dihydrogen peroxide; In acetic acid;	EXAMPLE 12 <strong>[110860-92-9]5,6-dichloro-3-pyridinol</strong>-1-oxide 3.28 g (20 mmol) of <strong>[110860-92-9]5,6-dichloro-3-pyridinol</strong> in 15 ml of glacial acetic acid were N-oxidized at 100 C. using 2.14 g (21 mmol) of 35% hydrogen peroxide. When the reaction was complete, the mixture was neutralized, extracted with ethyl acetate and washed until neutral, and the solvent was removed by evaporation. Yield 85% Melting point 174-175 C.

Reference： [1]Patent: US4756739,1988,A
[2]Synthesis,1990,p. 604 - 608

10
[ 110860-92-9 ]
5.6-diiodo-3-pyridinol [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S257 - S259

11
[ 110860-92-9 ]
BocNHCH₂CH₂OH or BocNHCH₂CH₂OTs [ No CAS ]
[2-(5,6-dichloro-pyridin-3-yloxy)-ethyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3321 - 3324

12
[ 110860-92-9 ]
[2-(5,6-dichloro-pyridin-3-yloxy)-ethyl]-methyl-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3321 - 3324

13
[ 110860-92-9 ]
5,6-diiodo-3-[(1-tert-butoxycarbonyl-2(S)-azetidinyl)methoxy]pyridine [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S257 - S259

14
[ 5418-51-9 ]
[ 110860-92-9 ]

Reference： [1]Synthesis,1990,p. 499 - 501
[2]Patent: US6133253,2000,A

15
[ 22353-40-8 ]
[ 110860-92-9 ]

Reference： [1]Synthesis,1990,p. 499 - 501
[2]Tetrahedron Letters,2013,vol. 54,p. 2303 - 2307
[3]Patent: US6133253,2000,A

16
[ 22353-38-4 ]
[ 110860-92-9 ]

Reference： [1]Synthesis,1990,p. 499 - 501
[2]Patent: US6133253,2000,A

17
[ 98121-41-6 ]
[ 110860-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium nitrite; In sulfuric acid; water; toluene;	EXAMPLE 11 5,6-dichloro-3-pyridinol Process (a) 8.15 g (50 mmol) of <strong>[98121-41-6]3-amino-5,6-dichloropyridine</strong> were dissolved in 100 ml of 8N H2 SO4 and diazotized at 0 C. using 3.55 g (53 mmol) of sodium nitrite in 9 ml of water. The cold diazonium salt solution was added dropwise to 100 C. warm 60% strength sulfuric acid. After completion of the nitrogen elimination, the mixture was neutralized and extractively distilled using toluene. The dried toluene phase was concentrated by evaporation and the residue was recrystallized repeatedly from toluene. Melting point 184-185 C.

Reference： [1]Synthesis,1990,p. 499 - 501
[2]Patent: US4756739,1988,A
[3]Tetrahedron Letters,2013,vol. 54,p. 2303 - 2307
[4]Patent: WO2016/91731,2016,A1
[5]Patent: US6133253,2000,A

18
[ 110860-92-9 ]
[ 130115-96-7 ]

Reference： [1]Synthesis,1990,p. 604 - 608
[2]Synthesis,1990,p. 604 - 608

19
[ 110860-92-9 ]
[ 110878-40-5 ]

Reference： [1]Synthesis,1990,p. 604 - 608

20
[ 110860-92-9 ]
[ 130115-97-8 ]

Reference： [1]Synthesis,1990,p. 604 - 608

21
[ 110860-92-9 ]
[ 110860-97-4 ]

Reference： [1]Synthesis,1990,p. 604 - 608

22
[ 110860-92-9 ]
[ 130115-95-6 ]

Reference： [1]Synthesis,1990,p. 604 - 608

23
[ 110860-92-9 ]
[ 59378-81-3 ]
[ 186593-03-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of triphenylphosphine(2.6 g, 9.88 mmol) in THF (30 mL) was added diethyl azodicarboxylate (1.56 mL, 9.88 mmol) at 0C, and the reaction mixture was stirred for 0.5 hour. 1-BOC-(R)-pyrrolidinemethanol (2.0 g, 9.88 mmol) and 5,6-dichloropyridine-3-ol (1.35 g, 8.23 mmol: prepared from 2-hydroxy-5-nitropyridine according to the procedure of V. Koch and S. Schnatterer, Synthesis 1990, 499-501) were then added. The reaction mixture was slowly warmed up to room temperature overnight. The solvent was removed. and the residue was chromatographed on a silica gel column, eluting with EtOAc/hexane 1:6 to afford an oil (2.16 g). MS (CI/NH3) m/z 347, 349 (M+H)+, 364, 366 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) delta 1.47 (s, 9H), 1.85-2.05 (m, 4H), 3.35-3.45 (m, 2H), 3.85-4.2 (m, 3H), 7.35-7.45 (br d, 1H), 8.02 (d, J = 2.5 Hz, 1H).

Reference： [1]Patent: EP1047690,2004,B1 .Location in patent: Page 15

24
[ 628-17-1 ]
[ 110860-92-9 ]
[ 808747-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.0h;	A mixture of <strong>[110860-92-9]5,6-dichloro-3-pyridinol</strong> (600 mg, 3.7 mmol),KaCOs (1.52 g, 11 mmol), 1-iodopentane (1.24 g, 7.3 mmol) andDMF (6 mL) was stirred at room temperature for 3 hours. Themixture was diluted with EtOAc (20 mL) and washed with water(30 mL) and brine (2 x 30 mL) . The organic layer was dried(NaaSCU) and filtered. The residue was purified by columnchromatography (EtOAc/hexane 1/25) to give 2,3-dichloro-5-(pentyloxy)pyridine (580 mg) as a colorless oil.NMR (CDC13, 200 MHz): 0.94 (3H, t, J = 6.9 Hz), 1.29-1.50 (4H,m), 1.73-1.87 (2H, m), 3.99 (2H, t, J = 6.4 Hz), 7.32 (1H, d,J=2.8 Hz) , 7.99(1H, d, -J = 2.8 Hz) .MS: 234 (M+l).

Reference： [1]Patent: WO2004/108686,2004,A2 .Location in patent: Page 183

25
[ 110860-92-9 ]
[ 124-63-0 ]
[ 283163-86-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water;	Intermediate 1.7: 2,3-Dichloro-5-(methylsulfonyloxy)pyridine At 0 C., initially 7.9 g of triethylamine and then 8.5 g of methanesulfonyl chloride were added to 11.6 g of <strong>[110860-92-9]2,3-dichloro-5-hydroxypyridine</strong> in 150 ml of methylene chloride. The mixture was subsequently stirred at approximately 20 C. for 17 hours and then washed with 100 ml of water. The organic phase was dried over magnesium sulfate and then concentrated. The resulting crude product was purified by silica gel chromatography (mobile phase: ethyl acetate/cyclohexane (1:1)). Yield: 9.1 g.

Reference： [1]Patent: US6432880,2002,B1

26
[ 110860-92-9 ]
[ 161511-85-9 ]
[ 186593-06-6 ]

Yield	Reaction Conditions	Operation in experiment
39%	With triphenylphosphine; diethylazodicarboxylate;	109b. 5,6-Dichloro-3-(1-t-butyloxycarbonyl-2-(S)-azetidinylmethoxy)pyridine N-Boc-2-(S)-azetidinol from Example 7b (1.55 g, 8.28 mmol), triphenylphosphine (2.6 g, 9.94 mmol), DEAD (1.6 mL, 9.94 mmol), and 5,6-dichloro-3-hydroxypyridine (1.5 g, 9.10 mmol) were allowed to react as in Example 9. The crude product was chromatographed eluding with EtOAc:hexane (1:5) to give 1.08 g of a waxy solid, 39% yield. MS (CI) m/e 333 (M+H)+. 1 H NMR (CDCl3, 300 MHz) d 7.97 (d, J=2.8 Hz, 1H), 7.41 (d, J=2.8 Hz, 1H), 4.56-4.48 (m, 1H), 4.40-4.30 (m, 1H), 4.12 (dd, J=10.1, 2.7 Hz, 1H-), 3.95-3.82 (m, 2H), 2.42-2.22 (m, 2H), 1.42 (s, 9H).
39%	With triphenylphosphine; diethylazodicarboxylate;	109b. 5,6-Dichloro-3-(1-t-butyloxycarbonyl-2-(S)-azetidinylmethoxy)pyridine N-Boc-2-(S)-azetidinol from Example 7b (1.55 g, 8.28 mmol), triphenylphosphine (2.6 g, 9.94 mmol), DEAD (1.6 mL, 9.94 mmol), and 5,6-dichloro-3-hydroxypyridine (1.5 g, 9.10 mmol) were allowed to react as in Example 9. The crude product was chromatographed eluding with EtOAc:hexane (1:5) to give 1.08 g of a waxy solid, 39% yield. MS (CI) m/e 333 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta: 7.97 (d, J=2.8 Hz, 1H), 7.41 (d, J=2.8 Hz, 1H), 4.56-4.48 (m, 1H), 4.40-4.30 (m, 1H), 4.12 (dd, J=10.1, 2.7 Hz, 1H), 3.95-3.82 (m, 2H), 2.42-2.2 (m, 2H), 1.42 (s, 9H).

Reference： [1]Patent: US5914328,1999,A
[2]Patent: US5948793,1999,A

27
[ 110860-92-9 ]
[ 110860-85-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium hydroxide; In 1,4-dioxane; water;	EXAMPLE 3 5,6-dichloro-3-difluoromethoxypyridine Chlorodifluoromethane was passed at 50 C. into a mixture of 32.8 g (0.2 mol) of <strong>[110860-92-9]5,6-dichloro-3-pyridinol</strong> in 200 ml of 1,4-dioxane and 40 g (1 mol) of sodium hydroxide in 100 ml of water until starting material was no longer present. The further procedure was then carried out as described in Example 1. Yield 77% Boiling point 57-60 C./0.1 mbar

Reference： [1]Patent: US4756739,1988,A

28
[ 110860-92-9 ]
[ 110860-83-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In acetonitrile;	EXAMPLE 1 3-(2-chloro-1,1,2-trifluoroethoxy)-5,6-dichloropyridine Chlorotrifluoroethylene was passed into a mixture of 16.4 g (0.1 mol) of <strong>[110860-92-9]5,6-dichloro-3-pyridinol</strong> I/29 and 20 g (0.145 mol) of anhydrous potassium carbonate in 100 ml of absolute acetonitrile at 35 C. until starting material was no longer present. The solid was filtered off under suction, the solvent was removed by distillation, and the residue was taken up in ether and washed until neutral. After drying over MgSO4 and removal of the ether by distillation, the residue was distilled in a high vacuum. Yield 83% Boiling point 85 C./0.03 mbar

Reference： [1]Patent: US4756739,1988,A

29
[ 38768-95-5 ]
[ 110860-92-9 ]
[ 1012084-47-7 ]

Yield	Reaction Conditions	Operation in experiment
50%		Preparation I 5,6-Dichloro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside 5.1 g (37.5 mM) of zinc chloride are melted under reduced pressure, the melt is cooled under an inert atmosphere and then 12 ml of toluene, 12 ml of acetonitrile, 3 g of 4 A molecular sieve and 2.45 g (15 mM) of <strong>[110860-92-9]5,6-dichloro-3-pyridinol</strong> are added. The temperature of the mixture is brought to 90 C. and 3.78 g (37.5 mM) of triethylamine and 5.86 g (16.5 mM) of 2,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl bromide are added. The reaction medium is stirred at 90 C. for 20 minutes and is then cooled and filtered to remove the inorganic salts, which are washed with ethyl acetate. The combined organic phases are washed with a 0.5 N sodium hydroxide solution and then the pH is brought to a value of 3 using a 0.1 N hydrochloric acid solution. The organic phase is subsequently washed with a saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The product is crystallized from ethyl ether and the desired product is obtained in the form of a light brown solid with a yield of 50%. M.p.=128 C. [alpha]D27=-92 (c=0.23; CHCl3).

Reference： [1]Patent: US2009/182013,2009,A1 .Location in patent: Page/Page column 5-6

30
[ 110860-92-9 ]
[ 2032-35-1 ]
[ 1154579-30-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With caesium carbonate; In N,N-dimethyl acetamide; at 100℃; for 16.0h;Inert atmosphere;	Preparation of 2,3-dichloro-5-(2,2-diethoxyethoxy)pyridine Bromoacetaldehyde diethyl acetal (2.74 ml, 18.3 mmol) and cesium carbonate (9.93 g, 30.5 mmol) were added to an N,N-dimethylacetamide solution (10 ml) of <strong>[110860-92-9]5,6-dichloropyridin-3-ol</strong> (1.0 g, 6.10 mmol), and stirred under a nitrogen atmosphere at 100C for 16 hours. Saline solution and ethyl acetate were added to the reaction solution, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 11:1 to 9:1) to obtain 2,3-dichloro-5-(2,2-diethoxyethoxy)pyridine (1.51 g, yield: 88 %) as an orange oil.

Reference： [1]Patent: EP2221301,2010,A1 .Location in patent: Page/Page column 32

31
[ 110860-92-9 ]
[ 6482-24-2 ]
[ 1154580-76-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate; In N,N-dimethyl acetamide; at 80℃; for 5.0h;Inert atmosphere;	Preparation of 2,3-dichloro-5-(2-methoxyethoxy)pyridine 2-Bromoethyl methyl ether (0.44 ml, 4.57 mmol) and cesium carbonate (2.48 g, 7.62 mmol) were added to an N,N-dimethylacetamide solution (5 ml) of <strong>[110860-92-9]5,6-dichloropyridin-3-ol</strong> (500 mg, 3.05 mmol), and stirred under a nitrogen atmosphere at 80C for 5 hours. The reaction solution was cooled with ice, then ammonium chloride water and ethyl acetate were added, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 9:1) to obtain 2,3-dichloro-5-(2-methoxyethoxy)pyridine (573 mg, yield: 85 %) as an orange oil.

Reference： [1]Patent: EP2221301,2010,A1 .Location in patent: Page/Page column 64

32
[ 110860-92-9 ]
[ 1262860-71-8 ]

Reference： [1]Patent: WO2013/27188,2013,A1

33
[ 110860-92-9 ]
[ 1425842-80-3 ]

Reference： [1]Patent: WO2013/27188,2013,A1

34
[ 373-53-5 ]
[ 110860-92-9 ]
[ 1425842-73-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 0 - 120℃; for 0.583333h;	a) 2,3-Dichloro-5-fluoromethoxy-pyridine To a solution of <strong>[110860-92-9]5,6-dichloro-pyridin-3-ol</strong> [1 1860-92-9] (500 mg, 3.05 mmol) and K2C03 (632 mg, 4.57 mmol) in dry ACN (12 ml) was added fluoro-iodomethane (1.156 ml, 9.15 mmol) at 0 C. The light yellow suspension was stirred for 5 min at 0 C and then heated up to 120 C for 30 min. Saturated aq. NH4CI was added, followed by EtOAc. The organic layer was separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried with Na2S04, filtered and evaporated to give a brown oil. The crude material was directly used in the next step without further purification. HPLC: RtH2= 0.95 min; ESIMS [M+H]+ = 198.1 ; 1H-NMR (400 MHz, DMSO-c/6): delta 8.31 (dd, 1 H), 8.07 (d, 1 H), 6.05 (s, 1 H), 5.91 (s, 1 H).

Reference： [1]Patent: WO2013/27188,2013,A1 .Location in patent: Page/Page column 99

35
[ 110860-92-9 ]
C₂₄H₃₀ClN₅O₆ [ No CAS ]