116986-13-1|3-(Bromomethyl)picolinonitrile| Ambeed

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Structure of 116986-13-1

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Quality Control of [ 116986-13-1 ] Purity: 97% SDS Specification

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Product Details of [ 116986-13-1 ]

CAS No. :	116986-13-1
Formula :	C₇H₅BrN₂
M.W :	197.03
SMILES Code :	N#CC1=NC=CC=C1CBr
MDL No. :	MFCD09030110
InChI Key :	BSSLVCQAYWTRRC-UHFFFAOYSA-N
Pubchem ID :	10375450

Safety of [ 116986-13-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302+H312-H315-H319-H331-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P311
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Computational Chemistry of [ 116986-13-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	41.79
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.	1.6
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	1.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.7
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.	0.62
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	2.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.54

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.36
Solubility	0.861 mg/ml ; 0.00437 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.	-1.84
Solubility	2.87 mg/ml ; 0.0146 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	-3.37
Solubility	0.0837 mg/ml ; 0.000425 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.	-6.47 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)	2.13

Application In Synthesis of [ 116986-13-1 ]

* 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 [ 116986-13-1 ]

[ 116986-13-1 ] Synthesis Path-Downstream 1~35

1
[ 20970-75-6 ]
[ 116986-13-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-Bromosuccinimide; In tetrachloromethane; for 16h;Reflux;	EXAMPLE 75; N-Cl-chloro-S-Cl^-naphthyridin-delta-y^pyridin-S-yl)^- fluorobenzenesulfonamide; (1) 3-(bromomethyl)picolinonitrile.; (Some starting materials may be obtained from TCI America, Wellesley, MA) To a 100 mL round-bottomed flask was added 3- methylpicolinonitrile (2.36 g, 20.0 mmol), NBS (7.82 g, 43.9 mmol), and CCl4 (50 mL). The reaction mixture was stirred at reflux for 16 h. The mixture was cooled to room temperature. The solid was filtered and washed with 50% EtOAc/hexanes. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexane to give 3- (bromomethyl)picolinonitrile (2.56 g, 65.0% yield). MS (ESI pos. ion) m/z calc'd for CvH5BrN2: 196.0, 198.0; found 197.0, 199.0. 1H NMR (300 MHz, CHLOROFORM-;/) delta ppm 4.64 (s, 2 H) 7.54 (dd, J=8.04, 4.68 Hz, 1 H) 7.92 (dd, J=8.04, 1.61 Hz, 1 H) 8.66 (dd, J=4.75, 1.53 Hz, 1 H)
63%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Reflux;	A mixture of 3-methylpicolinonitrile (2 g, 16.9 mmol, 1.0 eq), NBS (3 g, 16.9 mmol, 1.0 eq) and BPO (41 1 mg, 1.7 mmol, 0.1 eq) in CCU (30 mL) was refluxed and stirred overnight. Then the mixture was cooled to rt and concentrated. The residue was diluted with water (50 mL), extracted with DCM (50 mLx3). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified on silica gel column (PE/EtOAc = 5/1) to afford 3-(bromomethyl)picolinonitrile as a brown solid (2.1 g, 63%).
46%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80℃; for 2h;	EXAMPLE 1; 3-Cycloheptyl-8-((2,6-dichlorophenoxy)methyl)H-imidazo[1,5-a]pyridine; Compound 1A: 3-(Bromomethyl)picolinonitrile To a solution of 3-methylpicolinonitrile (660 mg, 5.6 mmol) in 20 mL of carbon tetrachloride was added NBS (1 g, 5.6 mmol) and dibenzoyl peroxide (200 mg, 0.83 mmol) at RT. The reaction mixture was heated at 80 C. for 2 hr, and then cooled to RT. The resulting solid was filtered off, and the filtrate was concentrated under reduced pressure to provide a residue. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under reduced pressure to provide crude material. The crude material was purified via silica gel chromatography (10% ethyl acetate in hexanes) to provide compound 1A (510 mg, 46%) as a pale yellow oil. HPLC Rt (Method A): 1.72 min. LC/MS (m/z)=197 (M+H)+.

37%	With N-Bromosuccinimide; carbonic acid dimethyl ester; dibenzoyl peroxide; at 87℃; for 5h;	To a 500 mL single-neck round bottom flash fitted with a reflux condenser and a nitrogen outlet was added 10.1 g (86 mmol) 3-methylpicolinonitrile, 200 mL dimethyl carbonate, 18.2 g (103 mmol) N-bromosuccinimide and 2.1 g (8.5 mmol) benzoyl peroxide. The resulting reaction mixture was heated to 87 C and stirred for 5 h. Following this duration, the reaction mixture was cooled to ambient temperature and filtered, and the solid was rinsed with Et20. DCM was subsequently added to the filtrate and the resulting mixture was filtered. The combined organics were concentrated and the resulting semi-solid was purified by silica gel chromatography (2 x 330 g column, 5-35% EtOAc/Hexane) followed by reverse-phase HPLC (Waters Xbridge Prep C18 10 muetatauiota OBD, 50 x 250 mm column) to afford the title compound as a yellow solid (6.3 g, 32.0 mmol, 37% yield). LC-MS m/z 196.8 (M+H)+, 0.60 min (ret. time).
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In 1,2-dichloro-ethane; for 2h;Reflux;	General procedure: General Procedure for the Preparation of 7-Aza-5,6-dihydro-5-oxo-11H-indeno[1,2-c]isoquinolines 12-14 [0111] 3-Methylpicolonitrile (10, 3.0-4.0 g, 25.4-33.9 mmol, 1 equiv), NBS (6.78-9.04 g, 38.1-50.8 mmol, 1.5 equiv), and AIBN (0.42-0.56 g, 2.5-3.4 mmol, 0.1 equiv) were diluted with 1,2-dichloroethane (80-100 mL), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was concentrated to half its original volume, filtered, and the filtrate was concentrated to dryness to provide crude 11. Compound 11 was diluted with acetonitrile (100-125 mL). The appropriate homophthalic anhydride (5, 6, or 7, 6.8-12.4 g, 41.9-55.9 mmol, 1.65 equiv) was added, followed by triethylamine (18-24 mL, 127.0-169.5 mmol, 5 equiv), and the solution was heated at reflux for 10 h. The solution was allowed to cool to room temperature, and the precipitate was filtered and washed with hot acetonitrile (2×35 mL) to provide the described compound.

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751.
[2]Patent: WO2009/155121,2009,A2 .Location in patent: Page/Page column 126-127.
[3]Patent: WO2015/103317,2015,A1 .Location in patent: Page/Page column 184; 185.
[4]Patent: US2006/281750,2006,A1 .Location in patent: Page/Page column 26.
[5]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.
[6]Patent: WO2018/109649,2018,A1 .Location in patent: Page/Page column 185.
[7]Organic Letters,2017,vol. 19,p. 3895 - 3898.
[8]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.
[9]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 473 - 476.
[10]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 262 - 266.
[11]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.
[12]Patent: US2014/18360,2014,A1 .Location in patent: Paragraph 0111.

2
[ 108-98-5 ]
[ 116986-13-1 ]
[ 81109-81-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.

3
[ 116986-13-1 ]
[ 131747-56-3 ]

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 473 - 476.

4
[ 116986-13-1 ]
[ 108-95-2 ]
[ 81109-80-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.

Yield	Reaction Conditions	Operation in experiment
21%		EXAMPLE 8 COMPOUND 8: [3-(3,3"-Dimethyl-3',4',5',6'-tetrahydro-2'H-cis-[2,2';6',2"]terpyridin-1'-ylmethyl)-pyridin-2-yl]-methanol To a solution of 3-methylpicolinonitrile (700 mg, 5.93 mmol) in CCl4 (15 mL) was added recrystallized N-bromosuccinimide (1.21 g, 6.82 mmol), followed by glacial HOAc (0.34 mL, 1.0 eq), and AIBN (97 mg, 0.60 mmol). The resultant mixture was heated to 65 C. for 3 hours, 80 C. for 2 hours, and then cooled to room temperature. The mixture was filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by flash chromatography (Hexanes/EtOAc, 90:10 followed by 80:20) provided 3-bromomethyl-pyridine-2-carbonitrile (250 mg, 21%) as a white solid. 1H NMR (CDCl3) delta 4.63 (s, 2H), 7.55 (dd, 1H, J=8.0, 4.6 Hz), 7.93 (dd, 1H, J=7.9, 1.2 Hz), 8.64 (dd, 1H, J=4.8, 1.4 Hz).

6
meso-3,3"-dimethyl-1',2',3',4',5',6'-hexahydro-cis-[2,2';6',2"]terpyridine [ No CAS ]
[ 116986-13-1 ]
3-(3,3"-dimethyl-3',4',5',6'-tetrahydro-2'H-cis-[2,2';6',2"]terpyridin-1'-ylmethyl)-pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
133 mg (88%)	With Ki; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	Using General Procedure A: A solution of 3,3"-dimethyl-1',2',3',4',5',6'-hexahydro-cis-[2,2';6',2"]terpyridine (0.104 g, 0.39 mmol), <strong>[116986-13-1]3-bromomethyl-pyridine-2-carbonitrile</strong> (0.115 g, 0.58 mmol), KI (23 mg, 0.14 mmol), and DIPEA (0.15 mL, 0.86 mmol) in DMF (4 mL) was heated at 60 C. for 20 hours. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-CH3OH-NH4OH) provided 133 mg (88%) of 3-(3,3"-dimethyl-3',4',5',6'-tetrahydro-2'H-cis-[2,2';6',2"]terpyridin-1'-ylmethyl)-pyridine-2-carbonitrile as a tan solid.

References: [1]Patent: US2005/154201,2005,A1 .

7
[ 116986-13-1 ]
[ 55942-74-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.

8
[ 116986-13-1 ]
[ 55942-75-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.

9
[ 116986-13-1 ]
[ 55942-66-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.

10
[ 116986-13-1 ]
[ 55942-67-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3515 - 3521.

11
[ 116986-13-1 ]
[ 693271-65-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With caesium carbonate; sodium iodide; In acetone; for 4.5h;Heating / reflux;	Step 4: 2-{4-[2-(6, 7-DIFLUORO-QUINOLIN-2-YL)-ETHYL]-PHENOXYMETHYL}-BENZONITRILE. 1.0 G (5.0 mmol) of the compound from step 1,0. 077 G (0.5 MMOL) of sodium iodide, 1.6 G (5.0 MMOL) of caesium carbonate and 1.4 G (3.5 MMOL) of the previous compound in 23 ml of acetone are stirred at reflux temperature for 4. 5HR. Once cooled, the solids are filtered and the filtrate is concentrated giving 1.6 G (79 %) of a solid

References: [1]Patent: WO2004/43966,2004,A1 .Location in patent: Page 81.

12
[ 2037-31-2 ]
[ 116986-13-1 ]
[ 126570-66-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol;	A. 2-CYANO-3-(3-CHLOROPHENYLTHIOMETHYL)PYRIDINE STR45 To a stirred, cloudy solution of sodium methoxide (14.7 g, 0.27 mol) in methanol (450 mL), contained in a water bath, add a solution of 3-chlorothiophenol (39.5 g, 0.27 mol) in methanol (95 mL). To the resultant solution add a solution of <strong>[116986-13-1]2-cyano-3-(bromomethyl)pyridine</strong> (48.9 g, 0.25 mol) in methanol (195 mL), and stir the reaction mixture at room temperature for 1 h. Concentrate the reaction mixture under reduced pressure, add 500 mL of ether to the residue, stir, and filter to remove the sodium bromide. Evaporate ether under reduced pressure to obtain the title compound as an amber oil, which may be used without further purification.
	With sodium methylate; In methanol;	B. 2-Cyano-3-(3-chlorophenylthiomethyl)pyridine STR80 To a stirred, cloudy solution of sodium methoxide (14.7 g, 0.27 mol) in methanol (450 mL), contained in a water bath, add a solution of 3-chlorothiophenol (39.5 g, 0.27 mol) in methanol (95 mL). To the resultant solution add a solution of the title compound of Part A above (48.9 g, 0.25 mol) in methanol (195 mL), and stir the reaction mixture at room temperature for 1 h. Concentrate the reaction mixture under reduced pressure, add 500 mL of ether to the residue, stir, and filter to remove sodium bromide. Evaporate ether under reduced pressure to obtain the title compound as an amber oil, which may be used without further purification in the following ring-closure process (Part C).

References: [1]Patent: US5430032,1995,A .
[2]Patent: US5104876,1992,A .

13
[ 372-20-3 ]
[ 116986-13-1 ]
2-cyano-3-(3-fluorophenoxymethyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In ethanol; hexane;	Reference Example 1: 2-Cyano-3-(3-fluorophenoxymethyl)pyridine To a chilled solution of sodium ethoxide, prepared from 13.8 g of sodium metal and 240 ml of absolute ethanol, 56.9 ml of 3-fluorophenol was added and the mixture was stirred at room temperature for 30 minutes. Crude 3-bromomethyl-2-cyanopyridine (103 g) was added to the mixture at 5 C., and the mixture was reflexed for 2 hours. After being concentrated, the reaction mixture was diluted with ether, and the resultant insoluble materials were removed by filtration. The filtrate was washed with 10% aqueous sodium hydroxide solution and with water, dried over anhydrous sodium sulfate, and then concentrated. The residue was crystallized by trituration with a mixture of ether and n-hexane to yield 58.0 g of pale brown crystals, which were recrystallized from isopropyl ether to give pale yellow needles, mp 52-53 C. Analysis for C13 H9 FN2 O Calculated C, 68.42; H, 3.97; N, 12.27 Found C, 68.37; H, 4.03; N, 12.25.

References: [1]Patent: US5334594,1994,A .

14
Cs₂ CO₃ [ No CAS ]
[ 108-43-0 ]
[ 116986-13-1 ]
2-CYANO-3-(3-CHLOROPHENOXYMETHYL)PYRIDINE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; In diethyl ether; di-isopropyl ether; acetone;	B. 2-CYANO-3-(3-CHLOROPHENOXYMETHYL)PYRIDINE STR156 Stir a solution of the title compound of part A above (0.71 g, 3.6 mmol), NaI (54 mg, 0.1 eq) and Cs2 CO3 (1.17 g, 1.0 eq) in dry acetone (17 mL, dried over MgSO4) at room temperature for 5 minutes, then add 3-chlorophenol (463 mg) via a syringe. Reflux over an oil bath for 4.5 hours. Filter and wash the filtrate with dry acetone. Concentrate the filtrate, suspend in diethyl ether, and refilter to obtain a brown solid which is the title compound in crude form. Triturate with pentane, and resuspend in diisopropyl ether (40 mL) with charcoal, and heat on a steam bath. Filter and evaporate the solvent to obtain the title compound, which crystallizes to form a white solid (640 mg): m.p. 70-72 C.
	With sodium iodide; In diethyl ether; di-isopropyl ether; acetone;	B. 2-CYANO-3-(3-CHLOROPHENOXYMETHYL)PYRIDINE STR40 Stir a solution of the title compound of part A above (0.71 g, 3.6 mmol), NaI (54 mg, 0.1 eq) and Cs2 CO3 (1.17 g, 1.0 eq) in dry acetone (17 mL, predried over MgSO4) at room temperature for 5 minutes, then add 3-chlorophenol (463 mg) via a syringe. Reflux in an oil bath for 4.5 hours. Filter and wash the filtrate with dry acetone. Concentrate the filtrate, suspend in diethyl ether, and refilter to obtain a brown solid which is the title compound in crude form. Triturate with pentane, and resuspend in diisopropyl ether (40 mL) with charcoal, and heat on a steam bath. Filter and evaporate the solvent to obtain the title compound, which crystallizes to form a white solid (640 mg): m.p. 70-72 C.
	With sodium iodide; In diethyl ether; di-isopropyl ether; acetone;	B. 2-Cyano-3-(3-Chlorophenoxymethyl)pyridine STR27 Stir a solution of the title compound of part A above (0.71 g, 3.6 mmol), NaI (54 mg, 0.1 eq) and Cs2 CO3 (1.17 g, 1.0 eq) in dry acetone (17 mL, dried over MgSO4) at room temperature for 5 minutes, then add 3-chlorophenol (463 mg) via a syringe. Reflux over an oil bath for 4.5 hours. Filter and wash the filtrate with dry acetone. Concentrate the filtrate, suspend in diethyl ether, and refilter to obtain a brown solid which is the title compound in crude form. Triurate with pentane, and resuspend in diisopropyl ether (40 mL) with charcoal, and heat on a steam bath. Filter and evaporate the solvent to obtain the title compound, which crystallizes to form a white solid (640 mg): m.p. 70-72 C.

With sodium iodide; In diethyl ether; di-isopropyl ether; acetone;

B. 2-Cyano-3-(3-chlorophenoxymethyl)pyridine STR63 Stir a solution of the title compound of part A above (0.71 g, 3.6 mmol), NaI (54 mg, 0.1 eq) and Cs2 CO3 (1.17 g, 1.0 eq) in dry acetone (17 ml, dried over MgSO4) at room temperature for 5 minutes, then add 3-chlorophenol (463 mg) via a syringe. Reflux over an oil bath for 4.5 hrs. Filter and wash the filtrate with dry acetone. Concentrate the filtrate, suspend in diethyl ether, and refilter to obtain a brown solid which is the title compound in crude form. Triturate with pentane, and resuspend in diisopropyl ether (40 ml) with charcoal, and heat on a steam bath. Filter and evaporate the solvent to obtain the title compound, which crystallizes to form a white solid (640 mg, m.p. 70-72 C.).

References: [1]Patent: US5422351,1995,A .
[2]Patent: US5430032,1995,A .
[3]Patent: US5514687,1996,A .
[4]Patent: US5104876,1992,A .

15
[ 20970-75-6 ]
aza(bis)isobutyronitrile (ABIN) [ No CAS ]
[ 116986-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrachloromethane;	A. 2-CYANO-3-(BROMOMETHYL)PYRIDINE STR155 Combine 2-cyano-3-methylpyridine (11.8 g), N-bromosuccinimide (NBS) (26.8 g, 1.5 eq.) and aza(bis)isobutyronitrile (ABIN) (180 mg) in dry CCl4 (300 mL). Reflux the mixture overnight. Pour the mixture into water, basify with NaOH and extract with CH2 Cl2. Wash the organic portion with water, dry (Na2 SO4), filter and concentrate to obtain a liquid. Chromatograph the product, eluding with 30% diethyl ether in hexanes. Combine the appropriate fractions to obtain the mono bromo compound (5.01 g) as a yellowish solid: m.p. 41.5-42.5 C.
	With N-Bromosuccinimide; In tetrachloromethane;	A. 2-CYANO-3-(BROMOMETHYL)PYRIDINE STR39 Combine 2-cyano-3-methylpyridine (11.8 g), N-bromosuccinimide (NBS) (26.8 g, 1.5 eq.) and aza(bis)isobutyronitrile (ABIN) (180 mg) in dry CCl4 (300 mL). Reflux the mixture overnight. Pour the mixture into water, basify with NaOH and extract with CH2 Cl2. Wash the organic portion with water, dry (Na2 SO4), filter and concentrate to obtain a liquid. Chromatograph the product, eluding with 30% diethyl ether in hexanes. Combine the appropriate fractions to obtain the mono-bromo compound (5.01 g) as a yellowish solid: m.p. 41.5-42.5 C.
	With N-Bromosuccinimide; In tetrachloromethane;	A. 2-Cyano-3-(bromomethyl)pyridine STR26 Combine 2-cyano-3-methylpyridine (11.8 g), N-bromo-succinimide (NBS) (26.8 g, 1.5 eq.) and aza(bis)isobutyronitrile (ABIN) (180 mg) in dry CCl4 (300 mL). Reflux the mixture overnight. Pour the mixture into water, basify with NaOH and extract with CH2 Cl2. Wash the organic portion with water, dry (Na2 SO4), filter and concentrate to obtain a liquid. Chromatograph the product, eluding with 30% diethyl ether in hexanes. Combine the appropriate fractions to obtain the mono bromo compound (5.01 g) as a yellowish solid: m.p. 41.5-42.5 C.

References: [1]Patent: US5422351,1995,A .
[2]Patent: US5430032,1995,A .
[3]Patent: US5514687,1996,A .

16
[ 20970-75-6 ]
N-Bromosuccinimide ("NBS") [ No CAS ]
aza(bis)isobutyronitrile ("ABIN") [ No CAS ]
[ 116986-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrachloromethane;	A. 2-Cyano-3-(bromomethyl)pyridine STR62 Combine 2-cyano-3-methylpyridine (11.8 g), N-bromosuccinimide ("NBS") (26.8 g, 1.0 eq) and aza(bis)isobutyronitrile ("ABIN") (180 mg) in dry CCl4 (300 ml). Reflux the mixture. Pour the mixture into water, basify with NaOH and extract with CH2 Cl2. Wash the organic portion with water, dry, filter and concentrate to obtain a liquid. Chromatograph the product, eluding with diethyl ether/hexane (30%). Combine the appropriate fractions to obtain the mono bromo compound (5.01 g) as a yellowish solid.

References: [1]Patent: US5104876,1992,A .

17
[ 87-65-0 ]
[ 116986-13-1 ]
[ 916800-04-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In acetone; at 20℃; for 2h;	Compound 1B: 3-((2,6-Dichlorophenoxy)methyl)picolinonitrile To a solution of 2,6-dichlorophenol (620 mg, 3.8 mmol) in 5 mL of anhydrous acetone was added potassium carbonate (520 mg, 3.8 mmol) and compound 1A (500 mg, 2.54 mmol) at RT. The reaction mixture was stirred at RT for 2 hr, and the resulting solid was filtered off. The solvent was removed from the filtrate in vacuo to provide a residue. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated to provide crude material. The crude material was purified via silica gel chromatography using 10% ethyl acetate in hexanes to provide compound 1B (530 mg, 50%) as a white solid. HPLC Rt (Method A): 3.23 min. LC/MS (m/z)=279 (M+H)+ and 301 (M+Na)+.

References: [1]Patent: US2006/281750,2006,A1 .Location in patent: Page/Page column 26.

18
potassium cyanide [ No CAS ]
[ 116986-13-1 ]
[ 5912-34-5 ]

Yield	Reaction Conditions	Operation in experiment
28.9%	In methanol; at 20℃; for 6h;	(2) 3-(cyanomethyl)picolinonitrile.; To a 100 mL round-bottomed flask was added <strong>[116986-13-1]3-(bromomethyl)picolinonitrile</strong> (1.56 g, 7917 mumol), potassium cyanide (509 muL, 11876 mumol), MeOH (50 mL). The reaction mixture was stirred at room temperature for 6 h. the solvent was removed in vacuo and the residue was dissolved in EtOAc (50 mL), washed with water (10 mL), saturated NaCl (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 40% EtOAc/hexanes to give 3- (cyanomethyl)picolinonitrile (328 mg, 28.9% yield). MS (ESI pos. ion) m/z calc'd for C8H5N3: 143.0; found 144.0. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 4.06 (s, 2 H) 7.63 (dd, J=8.11, 4.75 Hz, 1 H) 8.01 - 8.08 (m, J=0.73 Hz, 1 H) 8.73 (dd, J=4.75, 1.39 Hz, 1 H)

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751.
[2]Patent: WO2009/155121,2009,A2 .Location in patent: Page/Page column 127.

19
[ 405058-36-8 ]
[ 116986-13-1 ]
C₂₉H₃₀N₆O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 262 - 266.

20
[ 116986-13-1 ]
1,7-naphthyridin-6-yl trifluoromethanesulfonate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751.
[2]Patent: WO2009/155121,2009,A2 .

21
[ 116986-13-1 ]
[ 1201843-32-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751.
[2]Patent: WO2009/155121,2009,A2 .

22
[ 116986-13-1 ]
[ 5912-36-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751.
[2]Patent: WO2009/155121,2009,A2 .

23
[ 116986-13-1 ]
[ 5912-35-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751.
[2]Patent: WO2009/155121,2009,A2 .

24
[ 288-32-4 ]
[ 116986-13-1 ]
[ 1311148-68-1 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.

25
[ 5653-42-9 ]
[ 116986-13-1 ]
[ 1324006-68-9 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

26
[ 36795-25-2 ]
[ 116986-13-1 ]
[ 1324006-69-0 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

27
[ 703-59-3 ]
[ 116986-13-1 ]
[ 1324006-67-8 ]

Yield	Reaction Conditions	Operation in experiment
2.49 g	With triethylamine; In acetonitrile; for 10h;Reflux;	General procedure: General Procedure for the Preparation of 7-Aza-5,6-dihydro-5-oxo-11H-indeno[1,2-c]isoquinolines 12-14 [0111] 3-Methylpicolonitrile (10, 3.0-4.0 g, 25.4-33.9 mmol, 1 equiv), NBS (6.78-9.04 g, 38.1-50.8 mmol, 1.5 equiv), and AIBN (0.42-0.56 g, 2.5-3.4 mmol, 0.1 equiv) were diluted with 1,2-dichloroethane (80-100 mL), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was concentrated to half its original volume, filtered, and the filtrate was concentrated to dryness to provide crude 11. Compound 11 was diluted with acetonitrile (100-125 mL). The appropriate homophthalic anhydride (5, 6, or 7, 6.8-12.4 g, 41.9-55.9 mmol, 1.65 equiv) was added, followed by triethylamine (18-24 mL, 127.0-169.5 mmol, 5 equiv), and the solution was heated at reflux for 10 h. The solution was allowed to cool to room temperature, and the precipitate was filtered and washed with hot acetonitrile (2×35 mL) to provide the described compound. RRN 47-Aza-5,6-dihydro-5-oxo-11H-indeno[1,2-c]isoquinoline (12) [0112] The general procedure provided the described compound as a gray solid (2.49 g, 31%): mp 267-269 C. IR (KBr) 3098, 1665, 1573, 1478, 767, and 756 cm-1; 1H NMR (DMSO-d6) delta 12.18 (s, 1H), 8.56 (dd, J=4.9 and 1.3 Hz, 1H), 8.30 (d, J=8.0 Hz, 1H), 8.02 (dd, J=7.5 and 1.1 Hz, 1H), 7.82-7.80 (m, 2H), 7.57-7.51 (m, 1H), 7.36 (dd, J=7.5 and 5.0 Hz, 1H), 3.94 (s, 2H); ESIMS m/z (rel intensity) 235 (MH+, 100). Anal. Calcd for C15H10N2O: C, 76.91; H, 4.30; N, 11.96. [0113] Found: C, 76.58; H, 4.16; N, 11.80.

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.
[2]Patent: US2014/18360,2014,A1 .Location in patent: Paragraph 0111; 0112; 0113.

28
[ 116986-13-1 ]
[ 1324006-70-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.
[2]Patent: US2014/18360,2014,A1 .

29
[ 116986-13-1 ]
[ 1324006-71-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

30
[ 116986-13-1 ]
[ 1324006-72-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

31
[ 116986-13-1 ]
[ 1324006-73-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.
[2]Patent: US2014/18360,2014,A1 .

32
[ 116986-13-1 ]
7-aza-5,6-dihydro-6-(3-dimethylaminopropyl)-2,3-dimethoxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline dihydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

33
[ 116986-13-1 ]
7-aza-5,6-dihydro-6-(3-dimethylaminopropyl)-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

34
[ 116986-13-1 ]
[ 1324006-76-9 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.
[2]Patent: US2014/18360,2014,A1 .

35
[ 116986-13-1 ]
[ 1324006-79-2 ]
C₁₈H₁₃BrN₂O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6106 - 6116.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Blaise Reaction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Preparation of Aldehydes and Ketones • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Ritter Reaction • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Thorpe-Ziegler Reaction

Related Functional Groups of
[ 116986-13-1 ]

Bromides

A126019 [156072-86-5]

5-Bromo-3-methylpicolinonitrile

Similarity: 0.88

A533306 [27224-09-5]

4-Bromoisoquinoline-1-carbonitrile

Similarity: 0.78

A100660 [1211523-71-5]

2-(2-Bromopyridin-3-yl)acetonitrile

Similarity: 0.78

A387216 [27063-90-7]

5-Bromo-2,3-dimethylpyridine

Similarity: 0.77

A200872 [886364-86-9]

5-Bromo-4-methylpicolinonitrile

Similarity: 0.76

Nitriles

A100712 [126570-65-8]

3-(Dibromomethyl)picolinonitrile

Similarity: 0.92

A126019 [156072-86-5]

5-Bromo-3-methylpicolinonitrile

Similarity: 0.88

A256432 [5912-34-5]

3-(Cyanomethyl)picolinonitrile

Similarity: 0.82

A533306 [27224-09-5]

4-Bromoisoquinoline-1-carbonitrile

Similarity: 0.78

A100660 [1211523-71-5]

2-(2-Bromopyridin-3-yl)acetonitrile

Similarity: 0.78

Related Parent Nucleus of
[ 116986-13-1 ]

Pyridines

A100712 [126570-65-8]

3-(Dibromomethyl)picolinonitrile

Similarity: 0.92

A126019 [156072-86-5]

5-Bromo-3-methylpicolinonitrile

Similarity: 0.88

A256432 [5912-34-5]

3-(Cyanomethyl)picolinonitrile

Similarity: 0.82

A100660 [1211523-71-5]

2-(2-Bromopyridin-3-yl)acetonitrile

Similarity: 0.78

A387216 [27063-90-7]

5-Bromo-2,3-dimethylpyridine

Similarity: 0.77

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CAS No.: 116986-13-1

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