154237-70-4|4-Bromo-3-cyanopyridine| Ambeed

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Quality Control of [ 154237-70-4 ] Purity: 95% SDS Specification

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Product Details of [ 154237-70-4 ]

CAS No. :	154237-70-4
Formula :	C₆H₃BrN₂
M.W :	183.01
SMILES Code :	BrC1=C(C=NC=C1)C#N
MDL No. :	MFCD08686971
InChI Key :	DMQBJRMKGVMOHX-UHFFFAOYSA-N
Pubchem ID :	22329522

Safety of [ 154237-70-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H315-H318-H335
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338
Class:	8(6.1)
UN#:	2923
Packing Group:	Ⅲ

Computational Chemistry of [ 154237-70-4 ] Show Less

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	0.0
Molar Refractivity	36.65
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.43
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	1.21
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.72
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.	0.56
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	2.02
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.23
Solubility	1.08 mg/ml ; 0.00588 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.	-1.58
Solubility	4.85 mg/ml ; 0.0265 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	-2.96
Solubility	0.199 mg/ml ; 0.00109 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.	-6.56 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)	1.59

Application In Synthesis of [ 154237-70-4 ]

* 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 [ 154237-70-4 ]
Downstream synthetic route of [ 154237-70-4 ]

[ 154237-70-4 ] Synthesis Path-Upstream 1~1

1
[ 154237-70-4 ]
[ 13600-43-6 ]

References: [1] Organic Letters, 2014, vol. 16, # 6, p. 1744 - 1747.

[ 154237-70-4 ] Synthesis Path-Downstream 1~35

1
[ 1401098-23-4 ]
[ 154237-70-4 ]
[ 1401098-09-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation;	Step A: tert-Butyl 4-((4-(3-Cyanopyridin-4-yl)cyclohex-3-enyloxy)methyl)piperidine-l- carboxylate (Compound 50).; To a mixture of tert-butyl 4-((4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex- 3-enyloxy)methyl)piperidine-l-carboxylate (175.5 mg, 0.292 mmol), <strong>[154237-70-4]4-bromonicotinonitrile</strong> (80 mg, 0.437 mmol), and 2 M Na2C03 (278 mu, 0.556 mmol), in 6 ml DMF (N2 was bubbled through it), tetrakis(triphenylphosphine)palladium(0) (16.84 mg, 0.015 mmol) was added. After heating under under microwave irradiation at 120C for 1 h, mixture was extracted with water and AcOEt. Organic phase was dried over MgS04, filtered, and concentrated. Residue was purified by biotage CC (hexane/ AcOEt gradient) to give tert-butyl 4-((4-(3-cyanopyridin-4- yl)cyclohex-3-enyloxy)methyl)piperidine-l-carboxylate (100.6 mg, 0.253 mmol, 87 % yield). Exact mass calculated for Czs^NsOs: 397.24, found: LCMS m/z = 398.4 (M+H+); lU NMR (400 MHz, CDCl3) 5 ppm 1.10-1.20 (m, 11H), 1.69-1.90 (m, 5H), 1.98-2.05 (m, 2H), 2.24-2.33 (m, 1H), 2.40-2.50 (m, 1H), 2.53-2.63 (m, 1H), 2.67-2.75 (m, 1H), 3.31-3.40 (m, 2H), 3.63-3.69 (m, 1H), 4.07-4.14 (m, 2H), 6.14-6.16 (m, 1H), 7.25 (d, = 5.3 Hz, 1H), 8.68 (d, J = 5.3 Hz, 1H), 8.82 (s, 1H).

References: [1]Patent: WO2012/135570,2012,A1 .Location in patent: Page/Page column 127.

2
[ 154237-70-4 ]
[ 1429747-37-4 ]
[ 1429746-72-4 ]

Yield	Reaction Conditions	Operation in experiment
2.6%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; Microwave irradiation;	175 mg of 2-[1-(2-fluorobenzyl)-1 H-indazol-3-yl]-5-methoxypyrimidin-4-amine (1- 1 1-1, 0.501 mmol, 1. eq.), 101 mg of <strong>[154237-70-4]4-bromopyridine-3-carbonitrile</strong> (0.551 mmol, 1.1 eq.), 1 15 mg of Tris(dibenzylideneacetone)dipalladium (0) (0.125 mmol, 0.25 eq.), 156 mg of 1 ,1'-binaphthalene-2,2'-diylbis(diphenylphosphane) (0.25 mmol, 0.5 eq), 144 mg of sodium 2-methylpropan-2-olate (97%) (1.503 mmol, 3 eq.) and 52 ml of Nu,Nu-dimethylformamide were stirred under nitrogen atmosphere for 30 minutes at 100 ? and 300 W in a CEM microwave. The reaction mixture was washed with half-saturated aqueous sodium chloride solution. The organic layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (hexane/ dichloromethane/ methanol) and preparative HPLC. A crystallisation from dichloromethane/methanol gave 5.8 mg (0.01 mmol, 2,6%) of the analytically pure target compound. 1 H-NMR (300MHz, DMSO-de): delta [ppm]= 4.04 (s, 3H), 5.76 (s, 2H), 7.08 - 7.26 (m, 4H), 7.28 - 7.46 (m, 2H), 7.75 (d, 1 H), 8.20 - 8.31 (m, 2H), 8.45 (s, 1 H), 8.68 (d, 1 H), 8.88 (s, 1 H), 9.23 (s, 1 H). LC-MS: retention time: 1.28 min MS ES + : 452.33 [M+H] +

References: [1]Patent: WO2013/50438,2013,A1 .Location in patent: Page/Page column 252; 253.

3
[ 154237-70-4 ]
[ 1429747-37-4 ]
[ 1429746-80-4 ]

References: [1]Patent: WO2013/50438,2013,A1 .

4
[ 154237-70-4 ]
[ 1429747-48-7 ]
[ 1429746-84-8 ]

Yield	Reaction Conditions	Operation in experiment
6.1%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18h;	50 mg of 4-amino-2-[1-(2-fluorobenzyl)-1 H-indazol-3-yl]pyrimidin-5-ol (1-11-1 , 0.149 mmol, 1. eq.) were dissolved in 3 ml of N,N-dimethylformamide. 103 mg of potassium carbonate (0.746 mmol, 5 eq.) and 32.8 mg of 4-bromopyridine-3- carbonitrile (0.179 mmol, 1.2 eq.) were added. The reaction mixture was stirred at 100 ? bath temperature for 18 hours. After cooling at room temperature the mixture was filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC and preparative TLC to yield 4.21 mg (0.01 mmol, 6.1%) of the analytically pure target compound.1 H-NMR (400MHz, DMSO-de): delta [ppm]= 5.75 (s, 2H), 7.10 - 7.25 (m, 4H), 7.29 - 7.37 (m, 1 H), 7.41 (ddd, 1 H), 7.76 (d, 1 H), 8.21 (s, 1 H), 8.30 (d, 1 H), 8.48 (d, 1 H), 8.65 (d, 1 H), 8.86 (s, 1 H), 8.90 - 9.03 (m, 1 H), 11.09 - 11.44 (m, 1 H).LC-MS: retention time: 1.13 min MS ES + : 438.32 [M+H] +

References: [1]Patent: WO2013/50438,2013,A1 .Location in patent: Page/Page column 261.

5
[ 766-96-1 ]
[ 154237-70-4 ]
[ 1560949-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 4h;Inert atmosphere;	To a solution of <strong>[154237-70-4]4-bromo-nicotinonitrile</strong> (1.10 g, 6.00 mmol) in DMF (20 ml) are added bis(triphenylphosphine)-palladium(ll)-chloride (211 mg, 0.30 mmol), copper(l) iodide (34 mg, 0.18 mmol), triethylamine (1.66 ml, 12.0 mmol) and 1-bromo-4-ethynyl-benzene (1.19 g, 6.6 mmol). The mixture is flushed with nitrogen, heated to 80C and stirred in a closed reaction vial at this temperature for 4 hours. The reaction mixture is allowed to cool to room temperature and partitioned between water and dichloromethane. The organic phase is washed with 1 N HCI, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 4-(4-bromo- phenylethynyl)-nicotinonitrile as light yellow powder; HPLC/MS 2.09 min (B), [M+H] 283/285.

References: [1]Patent: WO2014/23390,2014,A2 .Location in patent: Page/Page column 61-62.

6
[ 154237-70-4 ]
[ 1560949-48-5 ]

References: [1]Patent: WO2014/23390,2014,A2 .

7
[ 154237-70-4 ]
[ 1560949-49-6 ]

References: [1]Patent: WO2014/23390,2014,A2 .

8
[ 154237-70-4 ]
[ 1560948-79-9 ]

References: [1]Patent: WO2014/23390,2014,A2 .

9
(1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
[ 154237-70-4 ]
[ 13600-43-6 ]

References: [1]Organic Letters,2014,vol. 16,p. 1744 - 1747.

10
(1,1,2,2,2-pentafluoroethyl)(1,10-phenanthroline-κΝ1,κN10)-copper [ No CAS ]
[ 154237-70-4 ]
[ 1580464-72-7 ]

References: [1]Organic Letters,2014,vol. 16,p. 1744 - 1747.

11
[ 154237-70-4 ]
[ 536-74-3 ]
[ 118159-97-0 ]

Yield	Reaction Conditions	Operation in experiment
78%		3-Cyano-4-(phenylethynyl)pyridine (35). Copper(l) iodide (9.6 mg, 0.05 mmol), bis- (triphenylphosphine)palladium(ll) dichloride (29 mg, 0.025 mmol) and sodium ascorbate (9.9 mg, 0.05 mmol) were placed in a flask, which was degassed and filled with argon. Triethylamine (5.0 mL) was added, followed by <strong>[154237-70-4]4-bromo-3-cyanopyridine</strong> 34 (92 mg, 0.5 mmol) in tetrahydrofuran (5.0 mL). The mixture was stirred at 40C for 30 min. Phenylethyne (76.5 mg, 0.75 mmol) was added and the mixture was stirred at 40C for 10 h. Evaporation and chromatography (petroleum ether / ethyl acetate 3: 1) gave 3-cyano-4-(phenylethynyl)pyridine 35 (80 mg, 78%) as an off-white powder: mp 74-75C (lit.91 85-87C); IR vmax 2222 (C?N), 2150 (C?C), 1582 (C=CAr), 1495 (C=N) cm"1; 1H NMR (CDCI3) delta 7.39-7.43 (3 H, m, Ph 3,4,5-H3), 7.45 (1 H, d, J = 5.2 Hz, 5-H), 7.63 (2 H, d, J = 8.2 Hz, Ph 2,6-H2), 8.75 (1 H, d, J = 5.2 Hz, 6-H), 8.87 (1 H, s, 2-H); 13C NMR (CDCI3) (HSQC / HMBC) delta 83.50 (ethyne 2-C), 101.29 (ethyne 1-C), 1 1.74 (4-C), 1 15.54 (C?N), 120.76 (Ph 1-C), 125.06 (5-C), 128.59 (Ph 3,5-C2), 130.28 (Ph 4- C), 132.38 (Ph 2,6-C2), 134.87 (3-C), 152.40 (2-C), 152.68 (6-C); MS m/z 227.0569 (M + Na)+ (C14H8N2Na requires 227.0585).
78%		4-Bromo-3-cyanopyridine 27 (92 mg, 0.5 mmol) in THF (5 mL)was added to CuI (9.6 mg, 50 lmol), (Ph3P)4Pd (29 mg, 25 lmol)and Na ascorbate (9.9 mg, 50 lmol) in Et3N (5 mL) under Ar. Themixture was stirred at 40 C for 30 min. Phenylethyne 21a(76.5 mg, 0.75 mmol) was added and the mixture was stirred at40 C for 10 h. Evaporation and chromatography (petroleumether/EtOAc 3:1) gave 28a (80 mg, 78%) as an off-white powder:mp 74-75 C (lit.53 85-87 C); IR mmax 2222, 2150, 1582, 1495(C=N) cm1; 1H NMR (CDCl3) d 7.39-7.43 (3H, m, Ph 3,4,5-H3),7.45 (1H, d, J = 5.2 Hz, 5-H), 7.63 (2H, d, J = 8.2 Hz, Ph 2,6-H2),8.75 (1H, d, J = 5.2 Hz, 6-H), 8.87 (1H, s, 2-H); 13C NMR (CDCl3) d83.50 (ethyne 2-C), 101.29 (ethyne 1-C), 111.74 (4-C), 115.54(C?N), 120.76 (Ph 1-C), 125.06 (5-C), 128.59 (Ph 3,5-C2), 130.28(Ph 4-C), 132.38 (Ph 2,6-C2), 134.87 (3-C), 152.40 (2-C), 152.68(6-C); MS m/z 227.0569 (M+Na)+ (C14H8N2Na requires 227.0585).

References: [1]Patent: WO2014/87165,2014,A1 .Location in patent: Page/Page column 94.
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032.

12
[ 154237-70-4 ]
[ 536-74-3 ]
[ 92905-81-2 ]

References: [1]Patent: WO2014/87165,2014,A1 .

13
[ 154237-70-4 ]
[ 768-60-5 ]
3-cyano-4-(4-methoxyphenylethynyl)pyridine [ No CAS ]