[ CAS No. 885277-48-5 ] {[proInfo.proName]}

Name: 885277-48-5|Methyl 2-bromo-6-methylnicotinate|97%
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Quality Control of [ 885277-48-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 885277-48-5 ]

SDS Specification

Alternatived Products of [ 885277-48-5 ]

Product Details of [ 885277-48-5 ]

CAS No. :	885277-48-5	MDL No. :	MFCD08059327
Formula :	C₈H₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UWRNYQBIUUVTGB-UHFFFAOYSA-N
M.W :	230.06	Pubchem ID :	11241687
Synonyms :

Calculated chemistry of [ 885277-48-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.18
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	2.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.85
Solubility :	0.328 mg/ml ; 0.00142 mol/l
Class :	Soluble
Log S (Ali) :	-2.58
Solubility :	0.599 mg/ml ; 0.0026 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.35
Solubility :	0.103 mg/ml ; 0.000449 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 885277-48-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 885277-48-5 ]

* 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 [ 885277-48-5 ]
Downstream synthetic route of [ 885277-48-5 ]

[ 885277-48-5 ] Synthesis Path-Upstream 1~2

1
[ 53277-47-7 ]
[ 885277-48-5 ]

Reference： [1] Patent: US2010/144760, 2010, A1, . Location in patent: Page/Page column 31

2
[ 67-56-1 ]
[ 38116-61-9 ]
[ 885277-48-5 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 19, p. 4569 - 4576

[ 885277-48-5 ] Synthesis Path-Downstream 1~10

1
[ 67-56-1 ]
[ 38116-61-9 ]
[ 885277-48-5 ]

Yield	Reaction Conditions	Operation in experiment
79%		Phosphorus oxybromide (21.53 g, 75 mmol) was added to the stirred solution of 2-hydroxy-6- methylnicotinic acid (5 g, 32.7 mmol), pyridine (0.475 mL, 5.88 mmol) in chlorobenzene (100 mL) at room temperature under nitrogen. The reaction mixture was refluxed for 1 h and concentrated under vacuum before treating with an excess of cold methanol. The solution was stirred for an additional 1 h and again concentrated under vacuum. The residue was dissolved in water and pH was adjusted to ~8.0 by adding K2CO3 before extraction of the product with CH2CI2. The organic layer was washed with water and brine solution, dried over anhydrous Na2S04. Filtrate was evaporated completely under reduced pressure to give crude residue. The resulted crude compound was purified by flash column chromatography (100-200 silica mesh, eluent was 30% EtOAc in pet ether) to obtained methyl 2-bromo-6-methylnicotinate (6.1 g, 79% yield) as colorless oil. 1H NMR (400 MHz, CDCI3): d 8.00 (d, /= 7.6 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 3.94 (s, 3H), 2.59 (s, 3H); LCMS (ES) m/z 230.0 (M+H)+

Reference： [1]Patent: WO2019/149959,2019,A1 .Location in patent: Page/Page column 60
[2]Tetrahedron,2005,vol. 61,p. 4569 - 4576

2
[ 292638-85-8 ]
[ 885277-48-5 ]
[ 853179-76-7 ]

Yield	Reaction Conditions	Operation in experiment
43%		Na2C03 (8.43 g, 80 mmol) was added to a solution of <strong>[885277-48-5]methyl <strong>[885277-48-5]2-bromo-6-methylnicotinate</strong></strong> (6.1 g, 26.5 mmol) and methyl acrylate (6.08 mL, 67.1 mmol) in mixture of DMA (16.99 mL, 181 mmol) and toluene (55 mL) at room temperature. Then the reaction mixture was degassed for 15 min. Tri-r olyl phosphine (0.807 g, 2.65 mmol) and allylpalladium chloride dimer (0.4850 g, 1.326 mmol) were added and the reaction mixture was stirred at 115 C in sealed tube for 5 h. Filtered through pad of Celite, and the filtrate was concentrated under reduced pressure. The resultant crude compound was purified by flash column chromatography on 100-200 mesh silica gel using 20% EtO Ac/pet-ether as an eluent to obtained (///-methyl 2-(3-methoxy-3-oxoprop-l- en-l-yl)-6-methylnicotinate (3.30 g, 43.0% yield) as a colorless oil. 1H NMR (400 MHz, CDCE): d 8.53 (dd, /= 1.2, 15.2 Hz, 1H), 8.22 (d, /= 6.8 Hz, 1H), 7.20-7.11 (m, 2H), 3.94 (s, 3H), 3.82 (s, 3H), 2.60 (s, 3H). LCMS (ES) m/z 236.09 (M+H)+

Reference： [1]Tetrahedron,2005,vol. 61,p. 4569 - 4576
[2]Patent: WO2019/149959,2019,A1 .Location in patent: Page/Page column 60; 61

3
[ 885277-48-5 ]
[ 853179-88-1 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 4569 - 4576
[2]Patent: WO2019/149959,2019,A1

4
[ 885277-48-5 ]
[ 173064-91-0 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 4569 - 4576
[2]Patent: WO2019/149959,2019,A1

5
[ 7486-35-3 ]
[ 885277-48-5 ]
[ 1228430-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 20 - 95℃;Inert atmosphere;	To a solution of <strong>[885277-48-5]methyl 2-bromo-6-methyl-3-pyridinecarboxylate</strong> D60 (1.15 g) and Pd(Ph3P)4 (0.2 g, 0.173 mmol) in 1,4-Dioxane (10 ml) stirred under nitrogen at room temperature tributyl(ethenyl)stannane (1.74 g, 5.50 mmol) was added neat in one charge. The reaction mixture was stirred at microwave Personal Chemistry at 95 C. for 30 minutes. The solvent was removed to give the crude title compound. Under similar conditions another batch of D60 (100 mg) was processed to give the crude title compound. The two crudes were joined and purified by flash chromatography on silica (80 g column, gradient elution from Cy to Cy/EtOAc 4:6) to afford the title compound D61 (1.0 g). UPLC (Basic GEN_C): rt=0.73 minutes, peak observed: 178 (M+1). C10H11NO2 requires 177. 1H NMR (400 MHz, CDCl3) delta ppm 8.08 (d, 1H), 7.66 (dd, 1H), 7.12 (d, 1H), 6.52 (d, 1H), 5.59 (dd, 1H), 3.93 (s, 3H), 2.63 (s, 3H).

Reference： [1]Patent: US2010/144760,2010,A1 .Location in patent: Page/Page column 31

6
[ 53277-47-7 ]
[ 885277-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl bromide; at 160℃; for 0.333333h;Inert atmosphere;	To a stirred solution of methyl 2-chloro-6-methyl-3-pyridinecarboxylate D59 (500 mg) in propionitrile (2 ml) under nitrogen at room temperature bromotrimethylsilane (0.699 ml, 5.39 mmol) was added dropwise neat. The reaction mixture was heated at Microwave Personal Chemistry 20 min at 160 C. The solvent was removed to give the crude. Under similar conditions another batch of D59 (500 mg) was processed to give the crude title compound. The two crudes were joined and purified together by flash chromatography on silica gel (80 g column, Cy 100% to Cy/EtOAc 4:6) to give the title compound D60 (1.2 g). 1H NMR (400 MHz, CDCl3) delta ppm 8.02 (d, 1H), 7.20 (d, 1H), 3.96 (s, 3H), 2.62 (s, 3H)

Reference： [1]Patent: US2010/144760,2010,A1 .Location in patent: Page/Page column 31

7
(R)-4-(4-(3-ethynylcyclopent-2-en-1-yl)piperazin-1-yl)benzonitrile [ No CAS ]
[ 885277-48-5 ]
(R)-methyl 2-((3-(4-(4-cyanophenyl)piperazin-1-yl)cyclopent-1-en-1-yl)ethynyl)-6-methylnicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.90%	With bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 70 - 85℃; for 14h;Inert atmosphere;	To a stirred solution of <strong>[885277-48-5]methyl <strong>[885277-48-5]2-bromo-6-methylnicotinate</strong></strong> (US2010144760, 2.79 g, 12.1 1 mmol) in acetonitrile (50 ml) (degassed by N2 purge separately) was added bis(triphenylphosphine)palladium(II) chloride (1.063 g, 1.514 mmol). The reaction mixture was heated up to 70 C and diisopropyl ethyl amine (7.83 g, 60.6 mmol) was added slowly, followed by a solution of (R)-4-(4-(3-ethynylcyclopent-2- en- l-yl)piperazin- l-yl)benzonitrile (Compound lj, 2.8 g, 10.10 mmol) in acetonitrile (20 ml) was added slowly at the same temperature. The reaction mixture was heated and stirred at 80-85 C for 14 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was distilled under vaccum to dryness to obtain a crude product which was purified by column chromatography over silica gel (100-200 mesh) using 60-80% ethyl acetate in hexane as an eluent to obtain the title product (0.9 gm, 20.90 % yield). iH NMR (400 MHz, CDC13) delta 8.17 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.2 Hz, 1H), 6.90 - 6.87 (m, 2H), 6.36 (d, J = 2.3 Hz, 1H), 4.08 - 4.03 (m, 1H), 3.96 (s, 3H), 3.40 - 3.35 (m, 4H), 2.75 - 2.67 (m, 6H), 2.64 (s, 3H), 2.13 - 2.09 (m, 1H), 2.03 - 1.95 (m, 1H). MS: m/z 427.24 (M+l).

Reference： [1]Patent: WO2017/29601,2017,A1 .Location in patent: Page/Page column 108-109

8
[ 885277-48-5 ]
ethyl 2-(4-chloro-6-(2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yloxy)benzo[b]thiophen-3-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2019/149959,2019,A1

9
[ 885277-48-5 ]
2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol [ No CAS ]

Reference： [1]Patent: WO2019/149959,2019,A1

10
[ 885277-48-5 ]
5-chloro-2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/149959,2019,A1

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 885277-48-5 ] {[proInfo.proName]}

Quality Control of [ 885277-48-5 ]

Related Doc. of [ 885277-48-5 ]

Product Details of [ 885277-48-5 ]

Calculated chemistry of [ 885277-48-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 885277-48-5 ]

Application In Synthesis of [ 885277-48-5 ]

[ 885277-48-5 ] Synthesis Path-Upstream 1~2

[ 885277-48-5 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 885277-48-5 ]

Bromides

Esters

Related Parent Nucleus of [ 885277-48-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
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Related Parent Nucleus of
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