955370-07-7|2-(6-Bromopyridin-2-yl)ethanol| Ambeed

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Quality Control of [ 955370-07-7 ] Purity: 97% SDS Specification

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Product Details of [ 955370-07-7 ]

CAS No. :	955370-07-7
Formula :	C₇H₈BrNO
M.W :	202.05
SMILES Code :	OCCC1=NC(Br)=CC=C1
MDL No. :	MFCD10000073
InChI Key :	BUSVXLMCEYFMCS-UHFFFAOYSA-N
Pubchem ID :	46835713

Safety of [ 955370-07-7 ]

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

Computational Chemistry of [ 955370-07-7 ] 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	2.0
Num. H-bond donors	1.0
Molar Refractivity	42.87
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.82
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	1.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.38
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.	0.98
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	2.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.34
Solubility	0.916 mg/ml ; 0.00454 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.	-1.79
Solubility	3.26 mg/ml ; 0.0161 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	-3.12
Solubility	0.154 mg/ml ; 0.000764 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.	-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	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)	1.81

Application In Synthesis of [ 955370-07-7 ]

* 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.

Downstream synthetic route of [ 955370-07-7 ]

[ 955370-07-7 ] Synthesis Path-Downstream 1~35

1
[ 955370-07-7 ]
4-(2,4-dichloro-5-methoxy-phenylamino)-6-methoxy-7-trimethylsilanylethynyl-quinoline-3-carbonitrile [ No CAS ]
4-(2,4-dichloro-5-methoxy-phenylamino)-7-[6-(2-hydroxy-ethyl)-pyridin-2-ylethynyl]-6-methoxy-quinoline-3-carbonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3993 - 3997.

2
2-(6-bromopyridin-2-yl)acetic acid methyl ester [ No CAS ]
[ 955370-07-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3993 - 3997.

3
ethyl(6-bromopyridin-2-yl)acetate [ No CAS ]
[ 955370-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride; In toluene; for 0.666667h;	2) Production of 2-(6-bromopyridin-2-yl)ethanol In a dry ice/acetone bath, 5.76 mL of 1.01 M diisobutylaluminium hydride/toluene solution was added to toluene (10 mL) solution of 355 mg of the compound obtained in the above reaction, and stirred for 40 minutes. Aqueous saturated ammonium chloride solution was added to the reaction liquid, extracted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. After concentrated under reduced pressure, the residue was purified through silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to obtain 123 mg of the entitled compound as a colorless oily substance. ESI-MS Found: m/z[M+H]+ 202, 204.

References: [1]Patent: US2007/254892,2007,A1 .Location in patent: Page/Page column 59.

4
[ 955370-07-7 ]
4-(2,4-dichloro-5-methoxy-phenylamino)-7-[6-(2-dimethylamino-ethyl)-pyridin-2-ylethynyl]-6-methoxy-quinoline-3-carbonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3993 - 3997.

5
[ 955370-07-7 ]
methanesulfonic acid 2-{6-[3-cyano-4-(2,4-dichloro-5-methoxy-phenylamino)-6-methoxy-quinolin-7-ylethynyl]-pyridin-2-yl}-ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3993 - 3997.

6
[ 955370-07-7 ]
4-(2,4-dichloro-5-methoxy-phenylamino)-6-methoxy-7-{6-[2-(4-methyl-piperazin-1-yl)-ethyl]-pyridin-2-ylethynyl}-quinoline-3-carbonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3993 - 3997.

7
[ 5315-25-3 ]
[ 68-12-2 ]
[ 955370-07-7 ]

Yield	Reaction Conditions	Operation in experiment
85%		Step GA solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 C. to a stirred solution of N,N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 C. for 15 min and then added at -78 C. to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 C. for 25 minutes and then N,N'-dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 C., methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride (1.1 g, 28 mmol) was added at -78 C. and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10% citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2×150 mL). The combined organic phase was dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using dichloromethane/acetone (95/5) to afford the title compound as pale yellow oil (5 g, 85%).1H-NMR (400 MHz, CDCl3): delta=3.01 (t, 2H), 3.09 (t, 1H), 4.02 (q, 2H), 7.16 (d, 1H), 7.34 (d, 1H), 7.43 (t, 1H)
85%		Step G; A solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 C to a stirred solution of N,N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 C for 15 min and then added at -78 C to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 C for 25 minutes and then N,N'-dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 C, methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride (1.1 g, 28 mmol) was added at -78 C and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10 % citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2 x 150 mL). The combined organic phase was dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using dichloromethane/acetone (95/5) to afford the title compound as pale yellow oil (5 g, 85 %). 1H-NMR (400 MHz, CDCl3): d = 3,01 (t, 2H), 3.09 (t, 1H), 4.02 (q, 2H), 7.16 (d, 1H), 7.34 (d, 1H), 7.43 (t, 1H)
85%		A solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 C to a stirred solution of N,N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 C for 15 min and then added at -78 C to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 C for 25 minutes and then Nu,Nu'- dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 C, methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride ( 1.1 g, 28 mmol) was added at -78 C and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10 % citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2 x 150 mL). The combined organic phase was dried over Na2S04, filtered and the solvents were removed. The residue was purified by chromatography on silica using dichloromethane/acetone (95/5) to afford the title compound as pale yellow oil (5 g, 85 %).-NMR (400 MHz, CDC13): d = 3.01 (t, 2H), 3.09 (t, 1H). 4.02 (q, 211), 7.16 (d, 1H). 7.34 (d, 1 H) 7.43 (t, 1 H)

76.5%

To a stirred solution of n-butyllithium (1 L, 1 .6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at -10 C under an N2 atmosphere for 30 minutes. The ice bath was removed and the reaction mixture was cooled to -78 C. A solution of 2-bromo-6-methyl pyridine (100 g, 0.58 mol) in THF ( .6 L) was added and the color changed pale yellow to dark brown. The mixture was stirred for 1 hour at the same temperature and then Lambda/,Lambda/'-dimethylformamide (200 mL, 2.147 mol) was added. After 60 minutes at -78 C, methanol (1.6 L) and acetic acid (160 mL, 2.49 mol) were added. Then sodium borohydride (28 g, 0.557 mol) was added at -78 C and the mixture was allowed to come to room temperature and was stirred overnight. The color changed dark brown to yellow color. The reaction mixture was diluted with ethyl acetate (3.0 L) and 10% citric acid solution (1.5 L) and was extracted with EtOAc (2 x 2L), and washed with brine (1 L). The combined organic extracts were dried over Na2S04 and solvents were removed under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/n-heptane (30/70) to afford the title compound as a pale yellow oil (90 g, 76.5%). 1H-NMR (400 MHz, CDCI3): delta = 7.43 (t, 1 H), 7.34 (d, 1 H), 7.16 (d, 1 H), 4.02 (q, 2H), 3.09 (t, 1 H), 3.01 (t, 2H)

References: [1]Patent: US2011/92537,2011,A1 .Location in patent: Page/Page column 25-26.
[2]Patent: EP2311823,2011,A1 .Location in patent: Page/Page column 26; 28.
[3]Patent: WO2011/45383,2011,A2 .Location in patent: Page/Page column 56.
[4]Patent: WO2015/110263,2015,A1 .Location in patent: Page/Page column 198.
[5]Journal of the American Chemical Society,2019,vol. 141,p. 15494 - 15497.
[6]Angewandte Chemie - International Edition,2019,vol. 58,p. 13942 - 13947.
Angew. Chem.,2019,vol. 131,p. 14080 - 14085,6.

8
[ 955370-07-7 ]
[ 13154-24-0 ]
[ 1292954-95-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 16h;	Compound 20 (1.17 g, 5.79 mmol), prepared as described5 was dissolved in N,N?-dimethylformamide (30 mL) and imidazole (1.57g, 23.14 mmol) added. After the addition of chlorotriisopropylsilane (2.23 g, 11.57 mmol), the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with a 10 % citric acid solution (3 x 30 mL) and brine (30 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents removed. The residue was purified by chromatography on silica using ethyl acetate/n-heptane(5/95) to afford 21 as colorless liquid (1.8 g, 87 %). 1H-NMR (400 MHz, CDCl3): delta = 0.92-1.13 (m, 21H),3.00 (t, 2H), 4.08 (q, 2H), 7.22 (d, 1H), 7.33 (d, 1H), 7.45 (t, 1H).
83%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 16h;	Step HThe title compound from Step G above (5 g, 24.75 mmol) was dissolved in N,N'-dimethylformamide (100 mL) and imidazole (4.84 g, 74.25 mmol) was added. After the addition of chlorotriisopropylsilane (7.92 mL, 37.1 mmol), the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethylether (300 mL) and washed with a 10% citric acid solution (3×40 mL) and brine (100 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a colorless liquid (7.36 g, 83%).1H-NMR (400 MHz, CDCl3): d=0.92-1.13 (m, 21H), 3.00 (t, 2H), 4.08 (q, 2H), 7.22 (d, 1H), 7.33 (d, 1H), 7.45 (t, 1H)
83%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 16h;	Steps H; The title compound from Step G above (5 g, 24.75 mmol) was dissolved in N,N'-dimethylformamide (100 mL) and imidazole (4.84 g, 74.25 mmol) was added. After the addition of chlorotriisopropylsilane (7.92 mL, 37.1 mmol), the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethylether (300 mL) and washed with a 10 % citric acid solution (3 x 40 mL) and brine (100 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a colorless liquid (7.36 g, 83 %). 1H-NMR (400 MHz, CDCl3): d = 0.92-1.13 (m, 21H), 3.00 (t, 2H), 4.08 (q, 2H), 7.22 (d, 1H), 7.33 (d, 1H), 7.45 (t, 1H)

83%

With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 16h;

The title compound from Step G above (5 g, 24.75 mmol) w7as dissolved in N.N'- dimethylformamide (100 mL) and imidazole (4.84 g, 74.25 mmol) was added. After the addition of chlorotriisopropylsilane (7.92 mL, 37.1 mmol), the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethylether (300 mL) and washed with a 10 % citric acid solution (3 x 40 mL) and brine ( 100 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a colorless liquid (7.36 g, 83 %). 1H-NM (400 MHz, CDC13): d = 0.92-1.13 (m, 21H), 3.00 (t, 2H), 4.08 (q, 2H), 7.22 (d, I H), 7.33 (d, 1H), 7.45 (t, 1H)

References: [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3330 - 3335.
[2]Patent: US2011/92537,2011,A1 .Location in patent: Page/Page column 26.
[3]Patent: EP2311823,2011,A1 .Location in patent: Page/Page column 26; 28.
[4]Patent: WO2011/45383,2011,A2 .Location in patent: Page/Page column 56-57.

9
[ 955370-07-7 ]
[ 1292954-96-1 ]