[ CAS No. 170235-19-5 ] {[proInfo.proName]}

Name: 170235-19-5|Methyl 6-bromo-5-hydroxypicolinate|95%
Brand: Ambeed
SKU: A790003
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Quality Control of [ 170235-19-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 170235-19-5 ]

Product Details of [ 170235-19-5 ]

CAS No. :	170235-19-5	MDL No. :	MFCD09878491
Formula :	C₇H₆BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GAVHSGPZDJCNDR-UHFFFAOYSA-N
M.W :	232.03	Pubchem ID :	15281236
Synonyms :

Calculated chemistry of [ 170235-19-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.24
TPSA :	59.42 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	1.71
Log Po/w (WLOGP) :	1.34
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	1.41
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.591 mg/ml ; 0.00255 mol/l
Class :	Soluble
Log S (Ali) :	-2.57
Solubility :	0.62 mg/ml ; 0.00267 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.39
Solubility :	0.954 mg/ml ; 0.00411 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.97

Safety of [ 170235-19-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 170235-19-5 ]

* 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 [ 170235-19-5 ]
Downstream synthetic route of [ 170235-19-5 ]

[ 170235-19-5 ] Synthesis Path-Upstream 1~1

1
[ 186581-53-3 ]
[ 178876-92-1 ]
[ 170235-19-5 ]
[ 170235-18-4 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633

[ 170235-19-5 ] Synthesis Path-Downstream 1~39

1
[ 358-23-6 ]
[ 170235-19-5 ]
[ 170235-20-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.5h;
95%	With 2,6-dimethylpyridine In dichloromethane for 0.0833333h; Ambient temperature;

Reference： [1]Ross Kelly; Lang, Fengrui [Tetrahedron Letters, 1995, vol. 36, # 30, p. 5319 - 5322]
[2]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

2
[ 170235-18-4 ]
[ 170235-19-5 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 5319 - 5322
[2]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633
[3]Patent: WO2014/78690,2014,A1 .Location in patent: Paragraph 00201

3
[ 186581-53-3 ]
[ 178876-92-1 ]
[ 170235-19-5 ]
[ 170235-18-4 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633

4
[ 1121-78-4 ]
[ 170235-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: Br₂ / pyridine / 77 h / Ambient temperature 2: 88 percent / K₂CO₃ / acetone / Heating 3: 77 percent / KMnO₄ / H₂O / 3 h / 90 °C 4: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature 5: 93 percent / AlCl₃ / CH₂Cl₂ / 48 h / Heating
	Multi-step reaction with 5 steps 1: sodium hydroxide; bromine / water 2: potassium carbonate / acetonitrile 3: potassium permanganate / water 4: triethylamine; dmap / dichloromethane 5: aluminum (III) chloride / dichloromethane

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]
[2]Current Patent Assignee: LUMIPHORE INC - WO2014/78690, 2014, A1

5
[ 24207-22-5 ]
[ 170235-19-5 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633
[2]Patent: WO2014/78690,2014,A1

6
[ 23003-35-2 ]
[ 170235-19-5 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633
[2]Patent: WO2014/78690,2014,A1

7
[ 54232-43-8 ]
[ 170235-19-5 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633
[2]Patent: WO2014/78690,2014,A1

8
[ 170235-19-5 ]
[ 170235-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 97 percent / Pd(PPh₃)2Cl₂ / dioxane / 100 °C 3: 95 percent / NBS / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature
	Multi-step reaction with 4 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 91 percent / Pd(PPh₃)2Cl₂ / dioxane / 12 h / 100 °C 3: NBS / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature 4: 10 percent / CrO₃, H⁺ / H₂O; ethyl acetate / 3 h

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]
[2]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

9
[ 170235-19-5 ]
[ 170235-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 97 percent / Pd(PPh₃)2Cl₂ / dioxane / 100 °C

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

10
[ 170235-19-5 ]
5,6-Divinyl-pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 89 percent / Pd(PPh₃)2Cl₂ / dioxane / 12 h / 100 °C

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

11
[ 170235-19-5 ]
[ 178876-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 91 percent / Pd(PPh₃)2Cl₂ / dioxane / 12 h / 100 °C

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

12
[ 170235-19-5 ]
6-Oxiranyl-5-trifluoromethanesulfonyloxy-pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 91 percent / Pd(PPh₃)2Cl₂ / dioxane / 12 h / 100 °C 3: NBS / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature 4: 55 percent / CrO₃, H⁺ / H₂O; ethyl acetate / 3 h

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

13
[ 170235-19-5 ]
[ 178876-96-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / Ambient temperature 2: 91 percent / Pd(PPh₃)2Cl₂ / dioxane / 12 h / 100 °C 3: NBS / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature

Reference： [1]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]

14
[ 1007170-24-2 ]
[ 170235-19-5 ]
[ 1007170-25-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 10h; Inert atmosphere;	4.3 4.3. Methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-hydroxypyridine-2-carboxylate Stir a solution of 37 g (163 mmol) of methyl 6-bromo-5-hydroxy-2-pyridine carboxylate and 51 g (196 mmol) of [3-(benzyloxy)-4-chlorophenyl]boronic acid in 300 mL of anhydrous DMF for 15 min while bubbling with argon, then add 63.8 g (196 mmol) of anhydrous caesium carbonate and 5 g (4.33 mmol) of Pd(PPh3)4. Stir the reaction mixture for 10 h at 90° C. under argon, cool to RT, then distribute in 1 L of ether/EtOAc 1:1 mixture and 1 L of a 0.5N aqueous HCl solution. Extract the aqueous phase again with 500 mL of EtOAc/ether 1:1 mixture. Combine the organic phases and wash with 4*500 mL of water. After drying over Na2SO4 and concentration under reduced pressure, take up the precipitate with 500 mL of a 7:3 mixture of pentane/DCM, filter and wash with pentane. We thus obtain 32 g of methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-hydroxypyridine-2-carboxylate in the form of yellow ochre powder. Yield 32 53%

Reference： [1]Current Patent Assignee: SANOFI - US2009/318473, 2009, A1 Location in patent: Page/Page column 19

15
[ 1180743-50-3 ]
[ 170235-19-5 ]
[ 1180743-51-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In 1,4-dioxane at 95℃; for 10h; Inert atmosphere;	1.3 Methyl 6-[3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]-5-hydroxypyridine-2-carboxylate 1.3 Methyl 6-[3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]-5-hydroxypyridine-2-carboxylate A solution of 80 g (345 mmol) of methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate and 146 g (499 mmol) of [3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]boronic acid in 1600 mL of anhydrous dioxane is stirred for 15 minutes while sparging with argon, followed by addition of 143 g (1034 mmol) of anhydrous K2CO3 and 14 g (17.2 mmol) of PdCl2(dppf). The reaction medium is stirred for 10 hours at 95° C. under argon, cooled to room temperature and then poured at room temperature into 2 L of EtOAc and 350 mL of aqueous 1N HCl solution. The organic phase is washed with 300 mL of aqueous 1N HCl solution and 600 mL of water. After drying over Na2SO4 and concentrating under reduced pressure, the precipitate is taken up in 500 mL of a 7/3 pentane/DCM mixture, filtered and washed with 200 mL of pentane. 105 g of methyl 6-[3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]-5-hydroxypyridine-2-carboxylate are thus obtained in the form of a brown powder, which is used without further purification in the following step. Yield=76%

Reference： [1]Current Patent Assignee: SANOFI - US2011/9426, 2011, A1 Location in patent: Page/Page column 10

16
[ 170235-19-5 ]
[ 623-48-3 ]
[ 1313404-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile Reflux;	1 To a mixture of 1 molar equivalent of methyl 2-bromo-3-hydroxy-6-pyridine carboxylate A (prepared as described in Kelly, T.R.; Lang, F. J. Org. Chem. 1996, 61, 4623-4633), potassium carbonate (3 molar equivalent), and anhydrous acetonitrile is added ethyl 2-iodoacetate (Aldrich Chemical Company, 1.5 molar equivalents). The resulting suspension is heated at reflux for several hours until the starting material is consumed as judged by thin layer chromatography. Solvent is removed by rotary evaporation, and the residue dissolved in dichloromethane and water. The solvents are separated, and the dichloromethane fraction concentrated by rotary evaporation and purified by silica gel column chromatography to yield compound B.

Reference： [1]Current Patent Assignee: LUMIPHORE INC - WO2011/79291, 2011, A1 Location in patent: Page/Page column 41

17
[ 170235-19-5 ]
[ 1313405-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / Reflux 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C 3.1: potassium hydroxide; water / tetrahydrofuran / 80 °C 3.2: pH 2 / Cooling in ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 °C

Reference： [1]Current Patent Assignee: LUMIPHORE INC - WO2011/79291, 2011, A1

18
[ 170235-19-5 ]
[ 1313405-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / Reflux 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C 3.1: potassium hydroxide; water / tetrahydrofuran / 80 °C 3.2: pH 2 / Cooling in ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 °C 5.1: potassium hydroxide; water / tetrahydrofuran / 20 °C 5.2: pH 2 / Cooling in ice

Reference： [1]Current Patent Assignee: LUMIPHORE INC - WO2011/79291, 2011, A1

19
[ 170235-19-5 ]
[ 1313405-04-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / Reflux 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C 3.1: potassium hydroxide; water / tetrahydrofuran / 80 °C 3.2: pH 2 / Cooling in ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 °C 5.1: potassium hydroxide; water / tetrahydrofuran / 20 °C 5.2: pH 2 / Cooling in ice 6.1: thionyl chloride / N,N-dimethyl-formamide / 1,4-dioxane / Reflux 6.2: Cooling in ice

Reference： [1]Current Patent Assignee: LUMIPHORE INC - WO2011/79291, 2011, A1

20
[ 170235-19-5 ]
[ 1313405-00-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / Reflux 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: LUMIPHORE INC - WO2011/79291, 2011, A1

21
[ 170235-19-5 ]
[ 1313405-01-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / Reflux 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C 3.1: potassium hydroxide; water / tetrahydrofuran / 80 °C 3.2: pH 2 / Cooling in ice
	Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 6 h / Reflux 2: sodium hydroxide / water; tetrahydrofuran / 5 h 3: trifluoroacetic acid; dihydrogen peroxide / water / 3 h / 80 °C / Inert atmosphere 4: potassium hydroxide / water / 36 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: LUMIPHORE INC - WO2011/79291, 2011, A1
[2]Current Patent Assignee: LUMIPHORE INC - WO2014/78690, 2014, A1

22
[ 5469-26-1 ]
[ 170235-19-5 ]
[ 1391846-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In acetone at 20℃;	3,85g (21 .55mmol) of 1 -bromopinacolone are added to 6-Bromo-5-hydroxy-pyridine- 2-carboxylic acid methyl ester (5,0g, 21 .55mmol) and Cesium carbonate (21 .06g, 64,65 mmol) in 100ml of acetone and the resulting mixture is stirred overnight at room temperature. The mixture is filtrated, the solvent removed in vacuo and the crude product obtained (6g, 84% yield) is used in the next step without further purification

Reference： [1]Current Patent Assignee: SANOFI - WO2012/101197, 2012, A1 Location in patent: Page/Page column 72

23
[ 170235-19-5 ]
[ 1391846-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / acetone / 20 °C 2: sodium hydroxide / methanol

Reference： [1]Current Patent Assignee: SANOFI - WO2012/101197, 2012, A1

24
[ 170235-19-5 ]
[ 1391846-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / acetone / 20 °C 2: sodium hydroxide / methanol 3: caesium carbonate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 24 h / 100 °C

Reference： [1]Current Patent Assignee: SANOFI - WO2012/101197, 2012, A1

25
[ 170235-19-5 ]
[ 1391846-41-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate / acetone / 20 °C 2: sodium hydroxide / methanol 3: caesium carbonate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 24 h / 100 °C 4: triethylamine; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Current Patent Assignee: SANOFI - WO2012/101197, 2012, A1

26
[ 170235-19-5 ]
[ 1610625-61-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 6 h / Reflux 2: sodium hydroxide / water; tetrahydrofuran / 5 h