[ CAS No. 97278-44-9 ] {[proInfo.proName]}

Name: 97278-44-9|Ethyl 6-(bromomethyl)picolinate|98%
Brand: Ambeed
SKU: A377214
Rating: 94 (30 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 97278-44-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 97278-44-9 ]

Product Details of [ 97278-44-9 ]

CAS No. :	97278-44-9	MDL No. :	MFCD09026929
Formula :	C₉H₁₀BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LEYJOYYSNHBEEE-UHFFFAOYSA-N
M.W :	244.09	Pubchem ID :	23033755
Synonyms :

Calculated chemistry of [ 97278-44-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.16
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.49
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	2.0
Log Po/w (MLOGP) :	1.43
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.69
Solubility :	0.497 mg/ml ; 0.00204 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.867 mg/ml ; 0.00355 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0415 mg/ml ; 0.00017 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.22

Safety of [ 97278-44-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 97278-44-9 ]

* 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 [ 97278-44-9 ]

[ 97278-44-9 ] Synthesis Path-Downstream 1~18

1
[ 97278-44-9 ]
[ 957114-93-1 ]
[ 892663-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In ethanol; toluene at 90℃; for 3h;	5 Description s; Ethyl 6-({5-chloro-2-[{2-meth l)-2-pyridinecarboxylate (D5); {5-Chloro-2-[(2-methylpropyl)oxy]phenyl}boronic acid (18g, 78mmol; may be prepared as described in D4), ethyl 6-(bromomethyl)-2-pyridιnecarboxylate (15.6g, 78mmol), potassium carbonate (43.2g, 312mmol) and Pd(PPh3)4 (9g, 0.78mmol) were stirred in 1 :1 toluene. ethanol ( 450 mL) under argon, at 900C, for 3 hours. The mixture was then cooled, some of the solvent was evaporated; the residue was diluted with water and extracted with diethyl ether. The organic phase was dried and evaporated The residue was purified by flash chromatography using 8%of ethyl acetate in hexane (9.3g). LCMS Rt = 3.73, [MH+] 348.1 , 350.1

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/128752, 2007, A1 Location in patent: Page/Page column 26

2
[ 39640-51-2 ]
[ 97278-44-9 ]

Yield	Reaction Conditions	Operation in experiment
32%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 84℃; Heating / reflux;	1 Intermediate 3: 6-(4-Iodo-phenoxymethyl)-pyridine-2-carboxylic acid ethyl ester Step 1: 6-Bromomethyl-pyridine-2-carboxylic acid ethyl ester Finely ground N-bromo-succinimide (29.4 g, 165.2 mmol) was added in several portions to a solution of 6-methyl-pyridine-2-carboxylic acid ethyl ester (24.7 g, 150.0 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in carbon tetrachloride (500 mL), and then benzoyl peroxide (100 mg, 0.4 mmol) was added. The mixture was heated at 84 degrees under nitrogen for approximately 40 h. Further portions of N-bromo-succinimide (14.8 g, 83.2 mmol) and then benzoyl peroxide (100 mg, 0.4 mmol) were added and heating was continued overnight. The reaction mixture was cooled to room temperature, filtered, evaporated, and purified by chromatography on silica gel using a Biotage system, eluding with 1:1 dichloromethane/hexane and dichloromethane to give 6-bromomethyl-pyridine-2-carboxylic acid ethyl ester (11.8 g, 32%) as a pale yellow oil. MS (MH+): 244/246. From HPLC, the purity was estimated at 85-90% and the material was used in the next step without further purification.
	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 14h; Heating / reflux;	198 Example 198; A mixture of 6-methyl-pyridine-2-carboxylic acid ethyl ester (1.65g, 10 mmol), NBS (1.77g, 10 mmol), and benzoyl peroxide (100 mg) in carbon tetrachloride (20ml) was refluxed for 14 h. After cooling to room temperature, the reaction mixture was.partitioned between diethyl ether and water (120ml, 4: 1), organic layer was washed with water (2X20 ml), brine, dried (MgS04), filtered and concentrated to give 6-bromomethyl-pyridine-2- carboxylic acid ethyl ester (2.4 g) which was used without further purification. LCMS m/z: 245 (M+1)+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2006/122256, 2006, A1 Location in patent: Page/Page column 22
[2]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/103022, 2005, A1 Location in patent: Page/Page column 130

3
[ 97278-44-9 ]
[ 24966-39-0 ]
[ 912934-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 2 - 10h;	3 To a solution of compound 13B in THF (10 mL/mmol) was added thiophenol (1 equiv.), DIEA (2 equiv.), and CsCO3 (1 equiv). The sealed reaction mixture was heated for 2-10 h at 60° C. to push the reaction to completion. The reaction was cooled to RT and diluted with hexane. The solid CsCO3 was removed by filtration, and the THF solvent was removed by rotary evaporation to yield compound 13C. LC/MS: m/z 342 (M+H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2006/235028, 2006, A1 Location in patent: Page/Page column 29

4
[ 41337-81-9 ]
[ 97278-44-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 6-(hydroxymethyl)pyridine-2-carboxylate With phosphorus tribromide In dichloromethane at 0℃; for 2h; Stage #2: With sodium hydrogencarbonate In dichloromethane	13 To a solution of compound 13A (2.86 g, 15.74 mmol) in DCM (100 mL) was added phosphorus tribromide (3.20 g, 11.80 mmol) at 0° C. The solution was stirred for 2 h at 0° C. under nitrogen, then quenched with 100 mL of saturated NaHCO3 solution. The DCM layer was separated, and the aqueous layer was extracted with DCM (3×100 mL). The combined extracts were washed with brine, dried over MgSO4, and evaporated to yield compound 13B (2.65 g). HPLC purity 93%. LC/MS: m/z 244 (M+H).
	With tetrabutylammomium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2006/235028, 2006, A1 Location in patent: Page/Page column 29
[2]Location in patent: scheme or table Labbe, Genevieve; Krismanich, Anthony P.; De Groot, Sarah; Rasmusson, Timothy; Shang, Muhong; Brown, Matthew D.R.; Dmitrienko, Gary I.; Guillemette, J. Guy [Journal of Inorganic Biochemistry, 2012, vol. 112, p. 49 - 58]

5
[ 97278-44-9 ]
[ 540-38-5 ]
[ 890051-45-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In acetone at 65℃;	2 Step 2: 6-(4-Iodo-phenoxymethyl)-pyridine-2-carboxylic acid ethyl ester 6-Bromomethyl-pyridine-2-carboxylic acid ethyl ester (1:1.72 g, 48 mmol; from Step 1 above) was dissolved in acetone (250 mL) and 4-iodophenol (11.61 g, 52.8 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) was added, followed by potassium carbonate (7.55 g, 54.6 mmol). The mixture was heated overnight at 65 degrees, and it was then cooled and filtered. The solid was washed with small portions of acetone and the filtrate was concentrated to approximately 100 mL by evaporation. The solution was warmed and then diluted with water (approximately 70 mL). The resulting brown solution was cloudy and started to precipitate an oily solid. The mixture was scratched with a spatula and allowed to cool to room temperature. The off-white precipitate was filtered off, washed with several portions of acetone/water (1:1), and then dried in vacuo over phosphorus pentoxide to give 6-(4-iodo-phenoxymethyl)-pyridine-2-carboxylic acid ethyl ester (13.72 g, 75%) as an off-white crystalline solid. MS (MH+) 384. 1H-NMR (CDCl3): δ 1.47 (t, 3H, J=7 Hz), 4.52 (q, 2H, J=7 Hz), 5.33 (s, 2H), 6.78 (d, 2H, J=9 Hz), 7.58 (d, 2H, J=9 Hz), 7.74 (d, 1H, J=7.8 Hz), 7.91 (dd, 1H, J=7.8, 7.8 Hz), 8.09 (d, 1H, J=7.8 Hz).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2006/122256, 2006, A1 Location in patent: Page/Page column 22

6
[ 97278-44-9 ]
[ 1004309-75-4 ]
[ 1004309-77-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In acetonitrile at 80℃; for 93h;

Reference： [1]Mameri, Samir; Charbonnière, Loïc; Ziessel, Raymond [Tetrahedron Letters, 2007, vol. 48, # 52, p. 9132 - 9136]

7
[ 97278-44-9 ]
[ 24677-78-9 ]
[ 590-17-0 ]
[ 863296-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2,3-dihydroxybenzaldehyde With sodium hydride In dimethyl sulfoxide for 0.166667h; Stage #2: 6-bromomethylpyridine-2-carboxylic acid ethylester In dimethyl sulfoxide for 1h; Stage #3: cyanomethyl bromide In dimethyl sulfoxide at 20℃; for 16h;	18 6-{2-Cyanomethoxy-3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-pyridine-2-carboxylic acid ethyl ester To 2,3-dihydroxybenzaldehyde (1 mmol) in dry DMSO (2.5 mL) is added NaH (60% suspension in oil, 2.5 mmol). After 10 minutes, 6-bromomethyl-pyridine-2-carboxylic acid ethyl ester (1 mmol) is added. After 1 hour, bromoacetonitrile (0.07 mL, 1 mmol) is introduced at ambient temperature and mixture is stirred for 16 hours. Saturated aqueous NH4Cl solution is used to quench the reaction and the mixture is extracted with EtOAc. After drying over sodium sulfate, solvent is removed. Purification of the mixture by preparative HPLC (20-70% MeCN/H2O) gives 6-(2-cyanomethoxy-3-formyl-phenoxymethyl)-pyridine-2-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 8.1 (d, J=7.7 Hz, 1H), 7.9 (t, J=7.9 Hz, 1H), 7.7 (d, J=8.2 Hz, 1H), 7.5 (dd, J=8.2, 2.4 Hz, 1H), 7.24 (m, 2H), 5.42 (s, 2H), 5.14 (s, 2H), 4.5 (q, J=7.2 Hz, 2H), 1.45 (t, J=7 Hz, 3H); LC/MS (ES+): 341.2 (M+1)+.

Reference： [1]Current Patent Assignee: IRM LLC - US2009/325981, 2009, A1 Location in patent: Page/Page column 16

8
[ 97278-44-9 ]
[ 1383979-16-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 140 °C 2: hydrogenchloride; water

Reference： [1]Labbe, Genevieve; Krismanich, Anthony P.; De Groot, Sarah; Rasmusson, Timothy; Shang, Muhong; Brown, Matthew D.R.; Dmitrienko, Gary I.; Guillemette, J. Guy [Journal of Inorganic Biochemistry, 2012, vol. 112, p. 49 - 58]

9
[ 97278-44-9 ]
[ 122-52-1 ]
[ 1401333-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 140℃;

Reference： [1]Location in patent: scheme or table Labbe, Genevieve; Krismanich, Anthony P.; De Groot, Sarah; Rasmusson, Timothy; Shang, Muhong; Brown, Matthew D.R.; Dmitrienko, Gary I.; Guillemette, J. Guy [Journal of Inorganic Biochemistry, 2012, vol. 112, p. 49 - 58]

10
[ 15658-60-3 ]
[ 97278-44-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: tetrabutylammomium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane

11
potassium cyanide [ No CAS ]
[ 97278-44-9 ]
[ 178265-40-2 ]