77332-79-7|3-Chloro-4-Iodopyridine| Ambeed

Structure of 77332-79-7

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Quality Control of [ 77332-79-7 ] Purity: 97% SDS Specification

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Product Details of [ 77332-79-7 ]

CAS No. :	77332-79-7
Formula :	C₅H₃ClIN
M.W :	239.44
SMILES Code :	ClC1=C(C=CN=C1)I
MDL No. :	MFCD00272199
InChI Key :	SQXBYRRNGPVSAU-UHFFFAOYSA-N
Pubchem ID :	12602200

Safety of [ 77332-79-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 77332-79-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	41.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.79
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	2.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.34
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.	2.01
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	3.05
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.26

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.22
Solubility	0.144 mg/ml ; 0.000601 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.	-2.03
Solubility	2.22 mg/ml ; 0.00929 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.6
Solubility	0.0606 mg/ml ; 0.000253 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.	-6.25 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	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)	1.67

Application In Synthesis of [ 77332-79-7 ]

* 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 [ 77332-79-7 ]
Downstream synthetic route of [ 77332-79-7 ]

[ 77332-79-7 ] Synthesis Path-Upstream 1~2

1
[ 626-60-8 ]
[ 77332-79-7 ]

Yield	Reaction Conditions	Operation in experiment
0.5 g	Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -75℃; for 4 h; Stage #2: With iodine In tetrahydrofuran at -75℃; for 1 h;	To a cold solution of 3-chloro pyridine (1.0 g, 8.88 mmol) in THF (30.0 mL) was added LDA (5.9 mL, 8.88 mmol) at -75°C. The reaction mixture was stirred at -75°C for 4 h. Iodine (2.2 g, 8.88 mmol) was added and continued stirring at -75°C for 1 h. The reaction mixture was quenched in water at -70°C, extracted with ethyl acetate and concentrated to afford 0.500 g of desired product. ¹H NMR (300 MHz, DMSO d₆): δ 8.01 (d, J = 5.1 Hz, 1H), 8.14 (d, / = 4.8 Hz, 1H), 8.63 (s, 1H).

References: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890.
[2] Tetrahedron Letters, 2004, vol. 45, # 42, p. 7873 - 7877.
[3] Tetrahedron, 1993, vol. 49, # 1, p. 49 - 64.
[4] Patent: US6169086, 2001, A, .
[5] Patent: WO2008/57209, 2008, A1, . Location in patent: Page/Page column 54-55.
[6] Patent: WO2008/18639, 2008, A2, . Location in patent: Page/Page column 108-109.
[7] Patent: WO2013/186692, 2013, A1, . Location in patent: Page/Page column 61; 62.

2
[ 626-60-8 ]
[ 77332-79-7 ]
[ 77332-90-2 ]
[ 77332-89-9 ]
[ 77332-88-8 ]

References: [1] Tetrahedron Letters, 1980, vol. 21, # 43, p. 4137 - 4140.
[2] Heterocycles, 1993, vol. 35, # 1, p. 151 - 169.
[3] Heterocycles, 1993, vol. 35, # 1, p. 151 - 169.
[4] Heterocycles, 1993, vol. 35, # 1, p. 151 - 169.

[ 77332-79-7 ] Synthesis Path-Downstream 1~36

1
[ 110-00-9 ]
[ 77332-79-7 ]
[ 40247-40-3 ]

References: [1]Heterocycles,1993,vol. 35,p. 151 - 169.

2
[ 110-00-9 ]
[ 77332-79-7 ]
[ 40247-40-3 ]
[ 77332-86-6 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 4137 - 4140.
[2]Heterocycles,1993,vol. 35,p. 151 - 169.

3
[ 626-60-8 ]
[ 77332-79-7 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate C8: 3-Chloro-4-phenylpyridin-2-olStep 1 : 3-Chloro-4-iodopyridineThe title compound was prepared according to the following reference: 35 Heterocvcles 151-69 (1993). To a solution of DIPA (3.77 mL, 26.4 mmol) in THF (20 mL) under N2 in a dry ice bath, M-BuLi (10.6 mL, 26.4 mmol) was added. The mixture was stirred in an ice bath for 20 minutes, then treated dropwise over 10 minutes with a solution of 3-chloropyridine (2.51 mL, 26.4 mmol) in 5 mL THF, keeping the temperature less than -70C. The lithiopyridine partially precipitated as a colorless solid in a light orange solution. The mixture was stirred for 30 minutes in a dry ice bath, and then I2 (6.71 g, 26.4 mmol) in 15 mL THF was added, keeping the temperature less then -650C. The solution was then allowed to warm to O0C and was placed in an ice bath for 2 hours, and then poured into 10% NaHSO3 and extracted with ether (150 mL; 3x). The organics were washed with 50 mL each OfNaHSO3, NaHCO3, H2O, and brine. The residue was purified on SiO2 (gradient elution, 2-20% EtOAc/hexanes) to give the title compound (3.35 g, 85% pure). This was then recrystallized EPO <DP n="56"/>from hot hexanes plus a few mL of EtOAc to dissolve initially to give the title compound as a white powder (1.95 g). LRMS ESf (M+H)+ 240.0.
		(A) Synthesis of 3-chloro-4-trifluoromethylpyridine-2- carboxylic acid; <n="110"/>(1) 3-Chloro-4-iodopyridine was obtained from 3-chloropgammaridine by the method described in Tetrahedron (1993.) 49 (1), 49.
0.5 g		To a cold solution of 3-chloro pyridine (1.0 g, 8.88 mmol) in THF (30.0 mL) was added LDA (5.9 mL, 8.88 mmol) at -75C. The reaction mixture was stirred at -75C for 4 h. Iodine (2.2 g, 8.88 mmol) was added and continued stirring at -75C for 1 h. The reaction mixture was quenched in water at -70C, extracted with ethyl acetate and concentrated to afford 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): delta 8.01 (d, J = 5.1 Hz, 1H), 8.14 (d, / = 4.8 Hz, 1H), 8.63 (s, 1H).

With n-butyllithium; iodine; diisopropylamine; sodium sulfite; In tetrahydrofuran; hexane;

1) Preparation of 3-Chloro-4-iodopyridine To 76 ml of an anhydrous THF solution of 10 ml of diisopropylamine was added 48.6 ml (1.57 M hexane solution) of n-butyllithium at -78 C., and the mixture was stirred at that temperature for 30 minutes. To the reaction mixture was added 10 ml of a THF solution of 8.66 g of 3-chloropyridine, followed by stirring at -78 C. for 30 minutes. To the reaction mixture was further added 30 ml of a THF solution of 19.4 g of iodine, followed by stirring at the same temperature for 30 minutes. The temperature was raised to 0 C., at which the mixture was stirred for 2.5 hours. The reaction mixture was poured into 300 ml of a 8% sodium sulfite aqueous solution and extracted with diethyl ether. The organic layer was washed successively with a 10% sodium hydrogencarbonate aqueous solution, water, and a saturated sodium chloride aqueous solution and dried. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using a mixture of ethyl acetate and hexane (1:9 by volume) as a developing solution. The fraction containing the desired compound was concentrated to give 4.54 g of the title compound. 1H-NMR (CDCl3) delta: 7.80 (d, 1H, J=5 Hz), 8.07 (d, 1H, J=5 Hz), 8.56 (s, 1H).

References: [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890.
[2]Tetrahedron Letters,2004,vol. 45,p. 7873 - 7877.
[3]Tetrahedron,1993,vol. 49,p. 49 - 64.
[4]Patent: WO2008/57209,2008,A1 .Location in patent: Page/Page column 54-55.
[5]Patent: WO2008/18639,2008,A2 .Location in patent: Page/Page column 108-109.
[6]Patent: WO2013/186692,2013,A1 .Location in patent: Page/Page column 61; 62.
[7]Patent: US6169086,2001,A .

4
[ 626-60-8 ]
[ 77332-79-7 ]
[ 77332-90-2 ]
[ 77332-89-9 ]
[ 77332-88-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 4137 - 4140.
[2]Heterocycles,1993,vol. 35,p. 151 - 169.
[3]Heterocycles,1993,vol. 35,p. 151 - 169.
[4]Heterocycles,1993,vol. 35,p. 151 - 169.

5
[ 625-86-5 ]
[ 77332-79-7 ]
[ 40247-42-5 ]

References: [1]Heterocycles,1993,vol. 35,p. 151 - 169.

6
[ 77332-79-7 ]
[ 146140-95-6 ]
2,2-dimethyl-N-(2-(3-chloro-4-pyridyl)phenyl)propanamide [ No CAS ]

References: [1]Tetrahedron,1993,vol. 49,p. 49 - 64.

7
[ 77332-79-7 ]
[ 81565-19-7 ]