[ CAS No. 937595-71-6 ]

Name: 937595-71-6|2-Chloro-3-Fluoropyridine-4-Boronic Acid|98%
Brand: Ambeed
SKU: A403035
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Product Details of [ 937595-71-6 ]

CAS No. :	937595-71-6	MDL No. :	MFCD04972403
Formula :	C₅H₄BClFNO₂	Boiling Point :	339.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	175.35 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 937595-71-6 ]

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 [ 937595-71-6 ]

Downstream synthetic route of [ 937595-71-6 ]

[ 937595-71-6 ] Synthesis Path-Downstream 1~15

1
[ 76-09-5 ]
[ 937595-71-6 ]
[ 1416367-16-2 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate In diethyl ether at 20℃; for 16h;

Reference： [1]Watson, Charlotte G.; Aggarwal, Varinder K. [Organic Letters, 2013, vol. 15, # 6, p. 1346 - 1349]

2
[ 937595-71-6 ]
[ 1453853-12-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 4.5 h / 80 °C / Inert atmosphere 1.2: 4 h 2.1: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,4-dioxane; water / 8 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; PFIZER INC - WO2013/130976, 2013, A1
[2]Ren, Li; Grina, Jonas; Moreno, David; Blake, James F.; Gaudino, John J.; Garrey, Rustam; Metcalf, Andrew T.; Burkard, Michael; Martinson, Matthew; Rasor, Kevin; Chen, Huifen; Dean, Brian; Gould, Stephen E.; Pacheco, Patricia; Shahidi-Latham, Sheerin; Yin, Jianping; West, Kristina; Wang, Weiru; Moffat, John G.; Schwarz, Jacob B. [Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1976 - 1991]

3
[ 937595-71-6 ]
[ 1453853-14-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 4.5 h / 80 °C / Inert atmosphere 1.2: 4 h 2.1: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube 3.1: hydrogenchloride / water-d2 / 10 h / 140 °C / Microwave irradiation
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,4-dioxane; water / 8 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube 3: hydrogenchloride / water / 10 h / 140 °C / Microwave irradiation

4
[ 937595-71-6 ]
[ 1453853-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 4.5 h / 80 °C / Inert atmosphere 1.2: 4 h 2.1: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube 3.1: hydrogenchloride / water-d2 / 10 h / 140 °C / Microwave irradiation 4.1: potassium hexamethylsilazane / tetrahydrofuran; 2-methyltetrahydrofuran / 0.17 h / 20 °C / Cooling with ice 4.2: 48 h / 80 - 90 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; PFIZER INC - WO2013/130976, 2013, A1

5
[ 937595-71-6 ]
[ 1453847-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 4.5 h / 80 °C / Inert atmosphere 1.2: 4 h 2.1: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube 3.1: hydrogenchloride / water-d2 / 10 h / 140 °C / Microwave irradiation 4.1: potassium hexamethylsilazane / tetrahydrofuran; 2-methyltetrahydrofuran / 0.17 h / 20 °C / Cooling with ice 4.2: 48 h / 80 - 90 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; PFIZER INC - WO2013/130976, 2013, A1

6
[ 3934-20-1 ]
[ 937595-71-6 ]
[ 1453853-10-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 2,6-Dichloropyrimidine; (2-chloro-3-fluoropyridin-4-yl)boronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 80℃; for 4.5h; Inert atmosphere; Stage #2: With dihydroxyborane for 4h;	21.A [003511 Step A: Sodium carbonate (2.13 g, 20.1 mmol) was added to 2-chloro-3- fluoropyridin-4-ylboronic acid (1.41 g, 8.05 mmol) and 2,4-dichloropyrimidine (1.0 g, 6.71 mmol) in 4:1 dioxane/water (50 mL), and the mixture was sparged with argon. PdC12(dppf)*DCM (0.274 g, 0.336 mmol) was added, and the mixture was heated at 80°C under argon. After 4.5 hours, more boronic acid (approximately 0.2 g) was added and heating continued for a total of 8.5 hours. The reaction mixture was diluted with water, and the resulting solid was collected by vacuum filtration to afford the desired 2-chloro-4-(2-chloro- 3-fluoropyridin-4-yl)pyrimidine (1.18 g, 4.84 mmol, 72.0% yield) with minor impurities.
72%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 80℃; for 8h; Inert atmosphere;

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; PFIZER INC - WO2013/130976, 2013, A1 Location in patent: Paragraph 00351
[2]Ren, Li; Grina, Jonas; Moreno, David; Blake, James F.; Gaudino, John J.; Garrey, Rustam; Metcalf, Andrew T.; Burkard, Michael; Martinson, Matthew; Rasor, Kevin; Chen, Huifen; Dean, Brian; Gould, Stephen E.; Pacheco, Patricia; Shahidi-Latham, Sheerin; Yin, Jianping; West, Kristina; Wang, Weiru; Moffat, John G.; Schwarz, Jacob B. [Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1976 - 1991]

7
[ 937595-71-6 ]
[ 1621911-92-9 ]
[ 1621912-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane at 100℃; for 12h; Sealed tube; Inert atmosphere;	2.2.1 Step 1 General procedure: To a sealed tube was added 6-chloro-7-((trans-4-methylcyclohexyl)methyl)-7H-purine- 2-carbonitrile (0.030 g, 0.10 mmol, Preparative Example 1.3), PdC dppfj-CFLC . adduct (0.025 g, 0.030 mmol), (2-chloro-3-fluoropyridin-4-yl)boronic acid (0.027 g, 0.016 mmol), K2CO3 (0.072 g, 0.52 mmol), and dioxane (1.0 mL). The reaction vessel was purged with argon, sealed, and heated at 100 °C for 12 hours. The completed reaction was diluted with DCM:MeOH (9: 1, 1.0 mL) and loaded onto a 2 g silica gel SPE cartridge and eluted with DCM:MeOH (9: 1, 20 mL). The organics were collected and concentrated under reduced pressure to afford 6-(2-chloro-3-fluoropyridin-4-yl)-7-((trans-4-methylcyclohexyl)methyl)-7H- purine-2-carbonitrile as a crude residue

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/123882, 2014, A1 Location in patent: Page/Page column 74

8
[ 937595-71-6 ]
1-(1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl)-3-fluoro-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,4-dioxane; water / 8 h / 80 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube 3.1: hydrogenchloride / water / 10 h / 140 °C / Microwave irradiation 4.1: potassium hexamethylsilazane / tetrahydrofuran; 2-methyltetrahydrofuran / 0.17 h / Cooling with ice 4.2: 48 h / 90 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h

Reference： [1]Ren, Li; Grina, Jonas; Moreno, David; Blake, James F.; Gaudino, John J.; Garrey, Rustam; Metcalf, Andrew T.; Burkard, Michael; Martinson, Matthew; Rasor, Kevin; Chen, Huifen; Dean, Brian; Gould, Stephen E.; Pacheco, Patricia; Shahidi-Latham, Sheerin; Yin, Jianping; West, Kristina; Wang, Weiru; Moffat, John G.; Schwarz, Jacob B. [Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1976 - 1991]

9
[ 937595-71-6 ]
1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-3-fluoro-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,4-dioxane; water / 8 h / 80 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / iso-butanol / 80 °C / Sealed tube 3.1: hydrogenchloride / water / 10 h / 140 °C / Microwave irradiation 4.1: potassium hexamethylsilazane / tetrahydrofuran; 2-methyltetrahydrofuran / 0.17 h / Cooling with ice 4.2: 48 h / 90 °C

10
[ 1138220-77-5 ]
[ 937595-71-6 ]
methyl 4-chloro-2-(2-chloro-3-fluoropyridin-4-yl)-5-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water Inert atmosphere; Reflux;	5.B Part B: Methyl 4-chloro-2-(2-chloro-3-fluoropyridin-4-yl)-5-methoxybenzoate A solution of (2-chloro-3-fluoropyridin-4-yl)boronic acid (3.45 g, 19.68 mmol), methyl 2-bromo-4-chloro-5-methoxybenzoate (5 g, 17.89 mmol), and K2CO3 (7.42 g, 53.7 mmol) in dioxane (40 mL) and water (15 mL) was purged with nitrogen gas 10 min. PdCl2(dppf)-CH2Cl2 adduct (1.46 g, 1.79 mmol) was added to the reaction mixture and again nitrogen gas was bubbled through the solution for another 10 min. The reaction mixture was heated to reflux overnight. The reaction mixture was then allowed to cool to room temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL) and filtered through diatomaceous earth (Celite). The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel chromatography (petroleum ether/EtOAc) to afford methyl 4-chloro-2-(2-chloro-3-fluoropyridin-4-yl)-5-methoxybenzoate (1.8 g, 5.45 mmol, 31% yield) as an off-white solid. LC/MS (ESI) m/e 329.8 [(M+H)+, calcd for C14H11Cl2NO3, 330.0]; LC/MS retention time (Method A2): tR=2.30 min; 1H NMR (400 MHz, DMSO-d6) δ 8.33 (d, J=5.0 Hz, 1H), 7.67 (m, 2H), 7.53 (t, J=5.3 Hz, 1H), 4.01 (s, 3H), 3.71 (s, 3H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2018/141956, 2018, A1 Location in patent: Paragraph 0158

11
[ 937595-71-6 ]
methyl 2-chloro-6-(3-fluoro-2-methylpyridin-4-yl)-3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 16 h / 95 °C / Inert atmosphere 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere