13472-61-2|5-Iodo-2-methoxypyridine| Ambeed

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Quality Control of [ 13472-61-2 ] Purity: 98% SDS Specification

COA

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Product Details of [ 13472-61-2 ]

CAS No. :	13472-61-2
Formula :	C₆H₆INO
M.W :	235.02
SMILES Code :	COC1=NC=C(I)C=C1
MDL No. :	MFCD07781180
InChI Key :	NTXRNCUPGYOZCN-UHFFFAOYSA-N
Pubchem ID :	23423786

Safety of [ 13472-61-2 ]

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

Computational Chemistry of [ 13472-61-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	43.45
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.15
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	1.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.69
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.	1.49
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	2.33
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.89

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.86
Solubility	0.321 mg/ml ; 0.00137 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.	-1.89
Solubility	3.0 mg/ml ; 0.0128 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	-3.11
Solubility	0.182 mg/ml ; 0.000776 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	Yes
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.	-6.45 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	0.0
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	1.0 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)	2.29

Application In Synthesis of [ 13472-61-2 ]

* 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 [ 13472-61-2 ]

[ 13472-61-2 ] Synthesis Path-Downstream 1~35

1
[ 504-29-0 ]
[ 13472-61-2 ]

References: [1]Chemische Berichte,1925,vol. 58,p. 116.
Chemisches Zentralblatt,1928,vol. 99,p. 64.

2
[ 20511-12-0 ]
[ 13472-61-2 ]

References: [1]Chemische Berichte,1925,vol. 58,p. 116.
Chemisches Zentralblatt,1928,vol. 99,p. 64.

3
[ 73290-22-9 ]
[ 67-56-1 ]
[ 13472-61-2 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333.

4
[ 13472-61-2 ]
[ 100-51-6 ]
[ 1083329-15-0 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333.

5
[ 1628-89-3 ]
[ 13472-61-2 ]

References: [1]Synthesis,2012,vol. 44,p. 735 - 746.

6
[ 13472-85-0 ]
[ 13472-61-2 ]

Yield	Reaction Conditions	Operation in experiment
81%		To an ice-cooled solution of isopropylmagnesium chloride (1.61 M inTHF, 4.64 mL, 7.47 mmol) in THF (20 mL) was slowly added n-BuLi(1.5 M in hexane, 4.98 mL, 7.47 mmol). The mixture was then stirred for 5 min to give a yellow solution, then 5-bromo-2-methoxypyridine (1.405 g, 0.98 mL, 7.10 mmol, 95%) was added and the resulting solution was stirred for 45 min at 0 C. Molecular iodine (3.79 g, 14.94 mmol) was added and the mixture was stirred for 30 min at 0 C then for 1 h at r.t. Sat. aq NH4Cl (5 mL) was then added, and the phases were separated. The aqueous phase was extracted with EtOAc (2 × 75mL) and the combined organic layers were dried over MgSO4, filtered,and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography (EtOAc-heptanes, 5-80%) to afford 4.

References: [1]Synthesis,2012,vol. 44,p. 735 - 746.
[2]Synthesis,2015,vol. 47,p. 3231 - 3240.
[3]Journal of the American Chemical Society,2015,vol. 137,p. 10480 - 10483.

7
[ 13472-61-2 ]
[ 105-53-3 ]
[ 902130-84-1 ]

References: [1]Synthesis,2013,vol. 45,p. 1475 - 1482.

8
[ 13472-61-2 ]
[ 178215-64-0 ]
3-(6-methoxypyridin-3-yl)-1-methyl-4-phenylquinolin-2(1H)-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2044 - 2054.

9
[ 13472-61-2 ]
[ 136281-10-2 ]
6-chloro-3-(6-methoxypyridin-3-yl)-1-methyl-4-phenylquinolin-2(1H)-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2044 - 2054.

10
[ 4319-49-7 ]
[ 13472-61-2 ]
C₁₀H₁₅N₃O₄S [ No CAS ]

References: [1]Chemical Science,2013,vol. 5,p. 222 - 228.

11
[ 13472-61-2 ]
C₁₃H₁₃NO₃S [ No CAS ]

References: [1]Chemical Science,2013,vol. 5,p. 222 - 228.

12
[ 13472-61-2 ]
[ 5720-07-0 ]
2-methoxy-5-(4'-methoxyphenyl)pyridine [ No CAS ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 3946 - 3954.

13
[ 13472-61-2 ]
[ 536-74-3 ]
[ 663955-53-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50℃; for 1.5h;Inert atmosphere;	To a 25-mL flask equipped with a magnetic stir bar and a condenser crowned with argon balloon, charged with a mixture of anhydrous DMF (4 mL) and <strong>[13472-61-2]5-iodo-2-methoxypyridine</strong> (0.99 g, 0.042 mmol), degassed for 2 h using a stream of argon slowly bubbled through the solution at rt. during vigorous stirring, phenylacetylene (0.055 mmol), Pd(PPh3)2Cl2 (38 mg), CuI (8 mg) were added. Subsequently anhydrous Et3N (1.5 mL) was added over 10 minutes and the mixture was heated at 50 C for 90 minutes. After this time the reaction mixture was cooled to rt. and aqueous saturated NaCl (10 mL) was added, the mixture was extracted with ethyl acetate (3 x 50 mL) and the combined organic layers were washed with brine (5 mL), dried over MgSO4 and filtered through the pad of Celite. Concentration in vacuo and purification by flash column chromatography (silica gel, n-hexane : ethyl acetate 9 : 1) yielded 1d in 90% yield as colourless oil.

References: [1]Tetrahedron,2014,vol. 70,p. 8624 - 8635.

14
[ 13472-61-2 ]
tert-butyl 2-((6-methoxypyridin-3-yl)sulfonyl)acetate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 10204 - 10208.
Angew. Chem.,2014,vol. 126,p. 10368 - 10372,5.

15
[ 13472-61-2 ]
[ 121-44-8 ]
C₆H₇NO₃S*C₆H₁₅N [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 10204 - 10208.
Angew. Chem.,2014,vol. 126,p. 10368 - 10372,5.

16
[ 13472-61-2 ]
[ 53279-93-9 ]
2-(6-methoxypyridin-3-yl)-4-phenylbutanenitrile [ No CAS ]
C₁₆H₁₆N₂O [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 10480 - 10483.

17
[ 13472-61-2 ]
[ 100-52-7 ]
[ 32401-35-7 ]

Yield	Reaction Conditions	Operation in experiment
93%		To a stirred solution of 3 (0.470 g, 2.00 mmol) in 2-MeTHF (30 mL) was added i-PrMgCl·LiCl (0.73 M in THF, 2.56 mL, 1.88 mmol) dropwise at r.t. Generation of the active nucleophile was followed by LCMS analysis by monitoring the dehalogenation after quenching in a vial of MeOH. After 75 min, benzaldehyde (0.251 g, 0.24 mL, 2.36 mmol) in 2-MeTHF (2 mL) was added and the mixture was immediately analyzed by LCMS, which showed full conversion of 3. Sat. aq. NH4Cl (5mL) was then added followed by H2O (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2 × 50 mL) and the organic layers were combined, washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (40 g SiO2; EtOAc-heptanes, 10-100%) followed by examination of the UV-active fractions by LCMS. The desired fractions were combined and concentrated to afford 6.

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

18
[ 13472-61-2 ]
(R_S)-N-{3-[(tert-butyldiphenylsilyl)oxy]propylidene}-2-methylpropane-2-sulfinamide [ No CAS ]
(R)-N-allylidene-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%		To a stirred solution of 3 (0.470 g, 2.00 mmol) in 2-MeTHF (30 mL) was added i-PrMgCl·LiCl (0.73 M in THF, 2.56 mL, 1.88 mmol) dropwise at r.t. Generation of the active nucleophile was followed by LCMS analysis by monitoring the dehalogenation after quenching in a vial of MeOH. After 75 min, 7 (554 mg, 1.33 mmol) in 2-MeTHF (1.6 mL) was added and the reaction mixture was stirred until the electrophile disappeared on LCMS (ca. 1.5 h; the solution became clear yellow), after which half-saturated aq NH4Cl (10 mL) was added and the phases were separated. The aqueous phase was extracted with EtOAc (2 × 50mL) and the organic layers were combined, washed with brine, dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (40 g SiO2; EtOAc-heptanes, 5-100%) followed by examination of the UV-active fractions by LCMS. Combination of UV-active fractions provided the byproduct 5.

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

19
[ 13472-61-2 ]
(R_S)-N-{3-[(tert-butyldimethylsilyl)oxy]propylidene}-2-methylpropane-2-sulfinamide [ No CAS ]
(R_S)-N-{(R)-3-[(tert-butyldimethylsilyl)oxy]-1-(6-methoxypyridin-3-yl)propyl}-2-methylpropane-2-sulfinamide [ No CAS ]
(R_S)-N-{(S)-3-[(tert-butyldimethylsilyl)oxy]-1-(6-methoxypyridin-3-yl)propyl}-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a solution of 4 (470 mg, 2.00 mmol) in 2-MeTHF (5 mL) was slowly added i-PrMgCl·LiCl (0.73 M in THF, 2.56 mL, 1.87 mmol) at r.t. Generation of the active nucleophile was followed by LCMS analysis and, after1 h, the solution was cooled to -10 C and diluted with CH2Cl2 (25mL), then (RS)-2 (389 mg, 1.33 mmol) in CH2Cl2 (5 mL) was added. The mixture was stirred for 5 h when LCMS indicated full conversion of the electrophile (RS)-2. The mixture became clear yellow, sat. aq. NH4Cl (5 mL) was added and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2 × 50 mL) and the organic layers were combined, concentrated in vacuo, and purified by silica gel chromatography (120 g SiO2; EtOAc-heptanes, 10-100%; eluting at ca. 60% EtOAc). The fractions containing the major isomer (as indicated by LCMS) were collected and evaporation of volatiles in vacuo at 60 C afforded the major isomer (RS,R)-3a.

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

20
[ 13472-61-2 ]
[ 1256375-11-7 ]
(S_S)-N-{(S)-3-[(tert-butyldimethylsilyl)oxy]-1-(6-methoxypyridin-3-yl)propyl}-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		To a solution of 4 (0.594 g, 2.53 mmol) in 2-MeTHF (6 mL) was added i-PrMgCl·LiCl (0.73 M in THF, 3.23 mL, 2.36 mmol) at -10 C. Generation of the active nucleophile was followed by LCMS analysis and, after1 h, the solution was diluted with CH2Cl2 (30 mL) at -10 C, then (SS)-2 (0.491 g, 1.69 mmol) in CH2Cl2 (5 mL) was added. The reaction mixture was stirred for 2.5 h followed by the addition of half-saturated aq NH4Cl (10 mL) and the phases were separated. The aqueous phase was extracted with CH2Cl2 (35 mL) and the organic phases were combined and concentrated in vacuo to provide a colorless oil that was subjected to purification by silica gel chromatography (40 g SiO2;EtOAc-heptanes, 10-80%; eluting at 63%) followed by examination of the UV-active fractions by LCMS analysis. The desired fractions were combined and concentrated in vacuo to provide the major isomer(SS,S)-3a.

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

21
[ 13472-61-2 ]
(S)-3-amino-3-(6-methoxypyridin-3-yl)propan-1-ol dihydrochloride [ No CAS ]

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

22
[ 13472-61-2 ]
(R)-3-amino-3-(6-methoxypyridin-3-yl)propan-1-ol dihydrochloride [ No CAS ]

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

23
[ 13472-61-2 ]
[ 1628-89-3 ]

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

24
[ 13472-61-2 ]
[ 1628-89-3 ]
[ 95881-82-6 ]

References: [1]Synthesis,2015,vol. 47,p. 3231 - 3240.

25
[ 13472-61-2 ]
4-[4-(2-methoxyphenyl)piperazin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
C₂₂H₂₃N₇O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1732 - 1737.

26
[ 13472-61-2 ]
[ 98-80-6 ]
C₁₂H₁₁NO₃S [ No CAS ]

References: [1]Chemical Science,2017,vol. 8,p. 3249 - 3253.

27
[ 13472-61-2 ]
[ 2114-36-5 ]
[ 5789-31-1 ]
2-methoxy-5-(1-phenylpropyl)pyridine [ No CAS ]
2-methoxy-5-(1-phenylpropyl)pyridine [ No CAS ]