867267-24-1|2,5-Dimethoxypyridine| Ambeed

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Quality Control of [ 867267-24-1 ] Purity: 95% SDS Specification

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Product Details of [ 867267-24-1 ]

CAS No. :	867267-24-1
Formula :	C₇H₉NO₂
M.W :	139.15
SMILES Code :	COC1=CN=C(OC)C=C1
MDL No. :	MFCD12546620
InChI Key :	HFFNRRVTKJCKGM-UHFFFAOYSA-N
Pubchem ID :	13433418

Safety of [ 867267-24-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 867267-24-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	37.22
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	31.35 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.11
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.69
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.1
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.28
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.08
Solubility	1.16 mg/ml ; 0.00833 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.96
Solubility	1.51 mg/ml ; 0.0109 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.25
Solubility	0.779 mg/ml ; 0.0056 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.95 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.1

Application In Synthesis of [ 867267-24-1 ]

* 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 [ 867267-24-1 ]

[ 867267-24-1 ] Synthesis Path-Downstream 1~35

1
[ 2591-86-8 ]
[ 867267-24-1 ]
[ 867267-25-2 ]
[ 867267-26-3 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1364 - 1376.
[2]Synlett,2005,p. 2080 - 2082.

2
[ 51834-97-0 ]
[ 74-88-4 ]
[ 867267-24-1 ]

References: [1]Synlett,2005,p. 2080 - 2082.
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1364 - 1376.

3
[ 867267-24-1 ]
[ 867267-34-3 ]

References: [1]Synlett,2005,p. 2080 - 2082.

4
[ 867267-24-1 ]
(Z)-2-Azido-3-(2,5-dimethoxy-pyridin-4-yl)-acrylic acid methyl ester [ No CAS ]

References: [1]Synlett,2005,p. 2080 - 2082.

5
[ 867267-24-1 ]
(Z)-2-Azido-3-(2,5-dimethoxy-pyridin-3-yl)-acrylic acid methyl ester [ No CAS ]

References: [1]Synlett,2005,p. 2080 - 2082.

6
[ 867267-24-1 ]
[ 867267-35-4 ]

References: [1]Synlett,2005,p. 2080 - 2082.

7
[ 867267-24-1 ]
4-chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2017/283412,2017,A1 .
[3]Patent: US2017/298052,2017,A1 .
[4]Patent: US2017/291892,2017,A1 .
[5]Patent: US2018/127401,2018,A1 .
[6]Patent: US2018/346424,2018,A1 .
[7]Patent: US2019/119213,2019,A1 .

8
[ 867267-24-1 ]
4-chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile [ No CAS ]

9
[ 867267-24-1 ]
tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate [ No CAS ]

10
[ 867267-24-1 ]
rac-tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2017/283412,2017,A1 .
[3]Patent: US2017/298052,2017,A1 .
[4]Patent: US2017/291892,2017,A1 .
[5]Patent: US2018/346424,2018,A1 .

11
[ 867267-24-1 ]
rac-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .
[3]Patent: US2017/283412,2017,A1 .
[4]Patent: US2017/283412,2017,A1 .
[5]Patent: US2017/298052,2017,A1 .
[6]Patent: US2017/291892,2017,A1 .
[7]Patent: US2018/346424,2018,A1 .

12
[ 867267-24-1 ]
methyl 2-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)imidazo[1,2-a]pyridine-6-carboxylate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .

13
[ 867267-24-1 ]
[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetic acid [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

14
[ 867267-24-1 ]
ethyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

15
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoic acid [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

16
[ 867267-24-1 ]
tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2018/346424,2018,A1 .

17
[ 867267-24-1 ]
rac-tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxybutanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2017/283412,2017,A1 .
[3]Patent: US2017/298052,2017,A1 .
[4]Patent: US2017/291892,2017,A1 .
[5]Patent: US2018/127401,2018,A1 .

18
[ 867267-24-1 ]
rac-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxybutanoic acid [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2017/283412,2017,A1 .
[3]Patent: US2017/298052,2017,A1 .
[4]Patent: US2017/291892,2017,A1 .
[5]Patent: US2018/127401,2018,A1 .

19
[ 867267-24-1 ]
tert-butyl 3-(trans-4-[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

20
[ 867267-24-1 ]
3-(trans-4-[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoic acid [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

21
[ 867267-24-1 ]
3-(trans-4-[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-(imidazo[1,2-a]pyridin-6-yl)propanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

22
[ 867267-24-1 ]
rac-tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(pyridin-2-yl)propanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2017/298052,2017,A1 .
[3]Patent: US2017/291892,2017,A1 .
[4]Patent: US2018/127401,2018,A1 .

23
[ 867267-24-1 ]
rac-tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1,3-oxazol-5-yl)propanoate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2017/298052,2017,A1 .
[3]Patent: US2017/291892,2017,A1 .
[4]Patent: US2018/127401,2018,A1 .

24
[ 867267-24-1 ]
2-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)imidazo[1,2-a]pyridine-6-carboxylic acid [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .

25
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-(imidazo[1,2-a]pyridin-6-yl)butanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .

26
[ 867267-24-1 ]
ethyl 6-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxybutanoyl}amino)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

27
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(trans-4-hydroxycyclohexyl)-N-(imidazo[1,2-a]pyridin-6-yl)propanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

28
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-(3-chloroimidazo[1,2-a]pyridin-6-yl)butanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .

29
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxy-N-(3-ethyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)butanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

30
[ 867267-24-1 ]
N-(3-butyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxybutanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .

31
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-(pyrazolo[1,5-a]pyridin-5-yl)butanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .

32
[ 867267-24-1 ]
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-(3-chloropyrazolo[1,5-a]pyridin-5-yl)butanamide [ No CAS ]

References: [1]Patent: US2016/272637,2016,A1 .
[2]Patent: US2016/272637,2016,A1 .

33
[ 867267-24-1 ]
[ 5419-55-6 ]
(2,5-dimethoxypyridin-4-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		66.9 g (661.1 mmol) of A/A-diisopropylamine were dissolved in 380 g of THF and cooled to a temperature of -60C. 395.2 mL (632.4 mmol) of w-butyllithium (1.6 M in hexane) were added within 45 min while keeping the temperature below -50C. The mixture was stirred at -60C for another 15 min. Then 80 g (574.9 mmol) of <strong>[867267-24-1]2,5-dimethoxypyridine</strong> were added within 45 min while keeping the temperature between -50 and -60C. After completion of the addition the adding funnel was washed with another 10 mL of THF. The reaction mixture was stirred at -60C for 2 h, before 118.9 g (632.4 mmol) triisopropyl borate was added within 30 min. Again the adding funnel was washed with 10 mL of THF. The reaction mixture was warmed to 20C and stirred for 30 min. Then a mixture of acetic acid (106 g) and water (602 g) was added within 15 min and the mixture was stirred for another 30 min. Then the organic solvents (650 g) were evaporated in vacuo (300 mbar) at a temperature of maximum 70C and the resulting suspension cooled to 20C and filtered. The product cake was washed with cold water (three times 100 mL) and dried at 40C for about 16 hours under reduced pressure in a drying oven. Yield: 78.6 g (75% of theory). MS (ESI+): m/z = 184.1 [M+H]+ ; 'H-NMR (400MHz, DMSO-cL): d [ppm] = 8.15 (hr s, 2H), 7.80 (s, 1H), 6.76 (s, 1H), 3.78 (d, 6H).
61%	With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20℃;	General procedure: At -78 C., lithium diisopropylamide (2 M in tetrahydrothranlheptane/ethylbenzene) was added to a solution of the appropriate pyridine derivative in tetrahydrofuran (3 ml/mmol), the mixture was stirred for 2-4 h and triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2-3 hand then slowly thawed to RT overnight. Afier addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.;11.53 g (82.9 mmol) of <strong>[867267-24-1]2,5-dimethoxypyridine</strong> were reacted according to General Method l. The desired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory)10599] LC/MS [Method 1]: R=0.47 mm; MS (ESIpos):mlz=184 (M+H).
61%		General procedure: 11,53 g (82.9 mmol) of <strong>[867267-24-1]2,5-dimethoxypyridine</strong> were reacted according to General Method 1A. Thedesired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory)LC/MS [Method 1]: R = 0.47 mm; MS (ESIpos): rnlz = 184 (M+H). At -78C, lithium diisopropylamide (2 M in tetrahydrofuran/heptane/ethylbenzene) was added to a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol), the mixturewas stirred for 2 to 4 h and triisopropyl borate was then added quickly. The reaction mixture was maintained at -78C for a further 2 to 3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off washed with waterand dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.

61%		General procedure: General Method 1A: Preparation of a Boronic Acid To a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuran/heptane/ethylbenzene), the mixture was stirred for 2-4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2-3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure. <strong>[867267-24-1]2,5-Dimethoxypyridin</strong>-4-ylboronic acid According to General Method 1A, 11.53 g (82.9 mmol) of <strong>[867267-24-1]2,5-dimethoxypyridine</strong> were reacted. The desired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory) LC/MS [Method 1]: Rt=0.47 min; MS (ESIpos): m/z=184 (M+H)+.
61%		General procedure: To a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuran/heptane/ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2 to 3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.
61%		General procedure: [0471] To a solution of the appropriate pyridine derivativein tetrahydroffiran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuranlheptane/ ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2 to 3 h and then slowly thawed to RT overnight. Afier addition of water, the tetrahydroffiran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.; According to General Method 1A, 11.53 g (82.9 mmol) of <strong>[867267-24-1]2,5-dimethoxypyridine</strong> were reacted. The desired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory) LC/MS [Method 1]: Rt=0.47 min; MS (ESIpos): m/z=184 (M+H)+
61%		General procedure: To a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuran/heptane/ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2 to 3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.
61%		To a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuranlheptane/ ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was added quickly. The reaction mixture was maintained at -78 C. for a thrther 2 to 3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydroffiran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered oil, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.
61%		General procedure: Lithium diisopropylamide (2M in tetrahydrofuran/heptane/ethylbenzene) was added to a solution of the corresponding pyridine derivative in tetrahydrofuran (ca. 3 ml/mmol) at -78 C., the mixture was stirred for 2 to 4 h and subsequently triisopropyl borate was added rapidly. The reaction mixture was maintained at -78 C. for a further 2 to 3h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), wherein a precipitate generally precipitated out, which was filtered, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium or magnesium sulfate), filtered and concentrated under reduced pressure.; Example 1.2A <strong>[867267-24-1]2,5-Dimethoxypyridin</strong>-4-ylboronic Acid 11.53 g (82.9 mmol) of <strong>[867267-24-1]2,5-dimethoxypyridine</strong> were reacted according to general method 1A. After acidification of the aqueous phase, the desired product precipitated out as a precipitate. Yield: 9.53 g (61% of theory) LC/MS [Method 1]: Rt=0.47 min; MS (ESlpos): m/z=184 (M+H)+.

References: [1]Patent: WO2019/175043,2019,A1 .Location in patent: Page/Page column 23-24.
[2]Patent: US2016/272637,2016,A1 .Location in patent: Paragraph 0485; 0597; 0598.
[3]Patent: WO2017/5725,2017,A1 .Location in patent: Page/Page column 60; 123.
[4]Patent: US2017/283412,2017,A1 .Location in patent: Paragraph 0321; 0436-0438.
[5]Patent: US2017/298052,2017,A1 .Location in patent: Paragraph 0465-0466; 0543-0545.
[6]Patent: US2017/291892,2017,A1 .Location in patent: Paragraph 0470; 0471; 0534; 0535; 0536.
[7]Patent: US2018/127401,2018,A1 .Location in patent: Paragraph 0478; 0479; 0530-0532.
[8]Patent: US2018/346424,2018,A1 .Location in patent: Paragraph 0429; 0430; 0447; 0448.
[9]Patent: US2019/119213,2019,A1 .Location in patent: Paragraph 0330; 0331; 0350; 0351; 0352.

34
[ 867267-24-1 ]
4-[5-chloro-2-(1,3-oxazol-5-yl)phenyl]-2,5-dimethoxypyridine [ No CAS ]

References: [1]Patent: WO2017/5725,2017,A1 .

35
[ 867267-24-1 ]
4-[5-chloro-2-(1,3-oxazol-5-yl)phenyl]-5-methoxypyridin-2(1H)-one [ No CAS ]

References: [1]Patent: WO2017/5725,2017,A1 .

Historical Records

Technical Information

• Nomenclature of Ethers • Preparation of Amines • Preparation of Ethers • Reactions of Ethers

Related Functional Groups of
[ 867267-24-1 ]

Ethers

A142359 [51834-97-0]

5-Hydroxy-2-methoxylpyridine

Similarity: 0.96

A104819 [18677-43-5]

2,4-Dimethoxypyridine

Similarity: 0.84

A157271 [66080-45-3]

2-Methoxypyridin-4-ol

Similarity: 0.84

A413139 [1628-89-3]

2-Methoxypyridine

Similarity: 0.83

A144309 [64436-92-6]

3-Amino-5-methoxypyridine

Similarity: 0.80

Related Parent Nucleus of
[ 867267-24-1 ]

Pyridines

A142359 [51834-97-0]

5-Hydroxy-2-methoxylpyridine

Similarity: 0.96

A104819 [18677-43-5]

2,4-Dimethoxypyridine

Similarity: 0.84

A157271 [66080-45-3]

2-Methoxypyridin-4-ol

Similarity: 0.84

A413139 [1628-89-3]

2-Methoxypyridine

Similarity: 0.83

A144309 [64436-92-6]

3-Amino-5-methoxypyridine

Similarity: 0.80

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CAS No.: 867267-24-1

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