Name: 1025735-46-9|3-(3,5-Dimethyl-1H-pyrazol-1-yl)phenylboronic acid|98%
Brand: Ambeed
SKU: A643442
Price: 35.0 USD
Availability: InStock
Rating: 96 (30 reviews)

1
[ 5292-43-3 ]
[ 1025735-46-9 ]
[ 1629249-85-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium phosphate; palladium diacetate; tris-(o-tolyl)phosphine In tetrahydrofuran for 22h; Inert atmosphere; Reflux;	35 tert-butyl 2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)acetate mixture of (3-(3,5-dimethyl-l pyrazol-l-yl)phenyl)boronic acid (Intermediate 9) (10.8 g, 50 mmol), fe/f-butyl 2-bromoacetate (14.6 g, 75 mmol), tri-o-tolylphosphine (1.5 g, 4.93 mmol), Pd(OAc)2 (700 mg, 3.12 mmol), powdered tripotassium phosphate (42.5 g, 200 mmol) and tetrahydrofuran (100 mL) was degassed under nitrogen/vacuum cycles and was heated at reflux for 16h. LCMS analysis shows ~ 70% conversion. Further palladium acetate (300 mg) and fe/f-butyl 2- bromoacetate (3 g) were added and the mixture was refluxed for 6 h. LCMS shows no starting material and the presence of product. The mixture was partitioned between water (200 mL) and EtOAc (2 x 200 mL) and the dried (MgS04). The organic phase was evaporated and the residue was purified by chromatography on a silica cartridge (330 g) eluting with 0-40% ethyl acetate- cyclohexane (15CV) to give the title compound (10.4 g, 72%) as a yellow oil: LCMS (Method C) RT=1.18 min, ES+ve m/z2S7 (M+H)+.
72%	Stage #1: bromoacetic acid <i>tert</i>-butyl ester; (3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)boronic acid With potassium phosphate; dichlorobis(tri-O-tolylphosphine)palladium In tetrahydrofuran for 16h; Inert atmosphere; Reflux; Stage #2: With palladium diacetate In tetrahydrofuran for 6h; Reflux;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1 Location in patent: Page/Page column 59
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

2
[ 5419-55-6 ]
[ 294877-29-5 ]
(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With n-butyllithium; In tetrahydrofuran; at -78℃; for 3.0h;Inert atmosphere;	A solution of l-(3-bromophenyl)-3,5-dimethyl-l pyrazole (intermediate 8) (30 g, 119 mmol) in THF (500 mL) was treated with triisopropyl borate (available from Avra) (41.6 mL, 179 mmol), cooled to -78 C, treated dropwise with 2.5 M nBuLi (119 mL, 299 mmol) over 1 h under argon, and stirred for 2 h at -78 C. The reaction mixture was quenched with aqueous HCI solution (2M, 150 mL), neutralised with 2M NaOH solution, and extracted with ethyl acetate (2 x 300 mL). The combined organic solutions were dried over Na2S04 and concentrated under reduced pressure. The residue was triturated with pentane and diethyl ether (1: 1) and the solid was collected by filtration to give the title compound '(15 g, 57%) as an off-white solid: MS ES+ve m/z 2l (M+H)+.

Reference： [1]Patent: WO2014/154725,2014,A1 .Location in patent: Page/Page column 33

3
[ 123-54-6 ]
[ 1025735-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / dichloromethane / 16 h / 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium acetate / ethanol / 2 h / Reflux 2: n-butyllithium; Triisopropyl borate / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

4
[ 1025735-46-9 ]
[ 1368456-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
	Multi-step reaction with 2 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

5
[ 1025735-46-9 ]
[ 1629249-86-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux
	Multi-step reaction with 3 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

6
[ 1025735-46-9 ]
[ 1629249-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C
	Multi-step reaction with 4 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

7
[ 1025735-46-9 ]
[ 1629249-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 4 °C / Cooling with ice
	Multi-step reaction with 6 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate 6: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0 °C / Cooling with ice
	Multi-step reaction with 5 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran / 2 h / 4 °C

Multi-step reaction with 6 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 16 h / 4 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]
[4]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

8
[ 1025735-46-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate
	Multi-step reaction with 5 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

9
[ 1025735-46-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate
	Multi-step reaction with 5 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

10
[ 1025735-46-9 ]
[ 1629249-91-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate 6: dihydrogen peroxide; lithium hydroxide / water; 2-methyltetrahydrofuran / 144 h / 0 °C / Cooling with ice
	Multi-step reaction with 5 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran / 2 h / 4 °C
	Multi-step reaction with 6 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 16 h / 4 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

11
[ 1025735-46-9 ]
[ 1629249-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C
	Multi-step reaction with 3 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

12
[ 1025735-46-9 ]
[ 1629249-93-9 ]
[ 1629249-94-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1

13
[ 1025735-46-9 ]
[ 1629249-95-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 4 °C / Cooling with ice 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C
	Multi-step reaction with 7 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5.1: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate 6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0 °C / Cooling with ice 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C
	Multi-step reaction with 6 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran / 2 h / 4 °C 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C

Multi-step reaction with 7 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 16 h / 4 °C 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]
[4]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

14
[ 1025735-46-9 ]
[ 1629249-96-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 4 °C / Cooling with ice 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C 7.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 120 h
	Multi-step reaction with 8 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5.1: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate 6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0 °C / Cooling with ice 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C 8.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 120 h
	Multi-step reaction with 7 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran / 2 h / 4 °C 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C 7.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 96 h

Multi-step reaction with 8 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 16 h / 4 °C 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C 8.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 96 h

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]
[4]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

15
[ 1025735-46-9 ]
[ 1629249-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 4 °C / Cooling with ice 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C 7.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 120 h 8.1: trifluoroacetic acid / chloroform / 2 h / 20 °C
	Multi-step reaction with 9 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5.1: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate 6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0 °C / Cooling with ice 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C 8.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 120 h 9.1: trifluoroacetic acid / chloroform / 2 h / 20 °C
	Multi-step reaction with 8 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran / 2 h / 4 °C 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C 7.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 96 h 8.1: trifluoroacetic acid / chloroform / 2 h / 20 °C

Multi-step reaction with 9 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 16 h / 4 °C 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C 8.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 96 h 9.1: trifluoroacetic acid / chloroform / 2 h / 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]
[4]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

16
[ 1025735-46-9 ]
[ 1629249-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / water; toluene / 5 h / 75 - 85 °C / Inert atmosphere; Large scale 2: hydrogen; rhodium contaminated with carbon / methanol / 26 h / 35 - 45 °C / 2250.23 Torr / Inert atmosphere; Large scale 3: silica thiol / methanol / 10 h / 60 - 70 °C / pH Ca_. 1 / Large scale 4: hydrogenchloride / acetonitrile; water / 0.67 h / 35 °C / Large scale 5: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C 3: hydrogenchloride; water / 2-methyltetrahydrofuran / 2 h / 40 °C 4: hydrogenchloride / acetonitrile; water / 0.67 h / 35 °C / Large scale 5: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C 3: hydrogenchloride / 2-methyltetrahydrofuran / 2 h / 40 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

17
[ 1025735-46-9 ]
[ 1629249-82-6 ]
[ 1629249-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: cyclopentyl methyl ether; hydrogenchloride / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 3.08 h / -78 - 20 °C 5.1: Chiralcel OD-H Column / hexane; isopropyl alcohol / Resolution of racemate 6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0 °C / Cooling with ice 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C 8.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 120 h 9.1: trifluoroacetic acid / chloroform / 2 h / 20 °C 10.1: borane-THF / tetrahydrofuran / 20 °C / Inert atmosphere 10.2: 4.25 h / 20 - 80 °C / Inert atmosphere
	Multi-step reaction with 9 steps 1.1: tris-(o-tolyl)phosphine; palladium diacetate; potassium phosphate / tetrahydrofuran / 22 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 4 °C / Cooling with ice 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C 7.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 120 h 8.1: trifluoroacetic acid / chloroform / 2 h / 20 °C 9.1: borane-THF / tetrahydrofuran / 20 °C / Inert atmosphere 9.2: 4.25 h / 20 - 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1

18
[ 1025735-46-9 ]
[ 1629249-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran; 2-methyltetrahydrofuran / 2 h / 5 °C / Cooling with ice; Inert atmosphere 3: hydrogen; 5% rhodium-on-charcoal / ethanol / 60 h
	Multi-step reaction with 3 steps 1.1: R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / 2-methyltetrahydrofuran; tetrahydrofuran / 2 h / 5 °C / Inert atmosphere 2.2: 0.5 h 3.1: rhodium contaminated with carbon / ethanol / 60 h

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

19
[ 1025735-46-9 ]
[ 1936434-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
	Multi-step reaction with 2 steps 1: R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

20
[ 1025735-46-9 ]
[ 1629249-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / water; toluene / 5 h / 75 - 85 °C / Inert atmosphere; Large scale 2: hydrogen; rhodium contaminated with carbon / methanol / 26 h / 35 - 45 °C / 2250.23 Torr / Inert atmosphere; Large scale 3: silica thiol / methanol / 10 h / 60 - 70 °C / pH Ca_. 1 / Large scale
	Multi-step reaction with 3 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C 3: hydrogenchloride; water / 2-methyltetrahydrofuran / 2 h / 40 °C
	Multi-step reaction with 3 steps 1: R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C 3: hydrogenchloride / 2-methyltetrahydrofuran / 2 h / 40 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

21
[ 1025735-46-9 ]
[ 2365406-14-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / water; toluene / 5 h / 75 - 85 °C / Inert atmosphere; Large scale 2: hydrogen; rhodium contaminated with carbon / methanol / 26 h / 35 - 45 °C / 2250.23 Torr / Inert atmosphere; Large scale 3: silica thiol / methanol / 10 h / 60 - 70 °C / pH Ca_. 1 / Large scale 4: hydrogenchloride / acetonitrile; water / 0.67 h / 35 °C / Large scale
	Multi-step reaction with 4 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C 3: hydrogenchloride; water / 2-methyltetrahydrofuran / 2 h / 40 °C 4: hydrogenchloride / acetonitrile; water / 0.67 h / 35 °C / Large scale
	Multi-step reaction with 4 steps 1: R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C 3: hydrogenchloride / 2-methyltetrahydrofuran / 2 h / 40 °C 4: hydrogenchloride / acetonitrile

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[3]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

22
[ 1025735-46-9 ]
[ 2365406-22-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / water; toluene / 5 h / 75 - 85 °C / Inert atmosphere; Large scale 2: hydrogen; rhodium contaminated with carbon / methanol / 26 h / 35 - 45 °C / 2250.23 Torr / Inert atmosphere; Large scale

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1

23
[ 1025735-46-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran; 2-methyltetrahydrofuran / 2 h / 5 °C / Cooling with ice; Inert atmosphere
	Multi-step reaction with 2 steps 1.1: R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / 2-methyltetrahydrofuran; tetrahydrofuran / 2 h / 5 °C / Inert atmosphere 2.2: 0.5 h

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

24
[ 1025735-46-9 ]
[ 1629249-48-4 ]
[ 1629249-50-8 ]
[ 1629249-99-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 45% 2: 4%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide In 1,4-dioxane at 90℃; for 1.16667h; Inert atmosphere;	13 tert-butyl 4-((R)-3-(2-(1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)-3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)butanoate A solution of (3-(3,5-dimethyl-lH-pyrazol-l-yl)phenyl)boronic acid (Intermediate 9) (44.7 g, 207 mmol) in KOH (3.8 M, 54.4 mL, 207 mmol) was treated with a solution of (/?,.r)-te/f-butyl 4-(3- (2-(l,8-naphthyridin-2-yl)ethyl)pyrrolidin-l-yl)but-2-enoate (Intermediate 12) (40 g, 103 mmol) in 1,4-dioxane (300 mL) and degassed several times using vacuum and nitrogen for 5 min. Chloro(l,5-cyclooctadiene)rhodium (I) dimer (2.55 g, 5.17 mmol) was added, followed by ( ?)-BINAP (6.44 g, 10.3 mmol) and the mixture was degassed for a further 5 min. The solution was heated at 90 °C for 60 min. After cooling, the reaction mixture was partitioned between DCM (250 mL) and water (200 mL). The aqueous phase was further extracted with DCM (200 mL) and the combined organic solutions were evaporated in vacuo. The residual oil (95 g) was dissolved in DCM and purified by chromatography on an aminopropyl cartridge KPNH (900 g) eluting with a gradient of 0- 50% ethyl acetate-cyclohexane over 10CV. The appropriate fractions were combined and evaporated in vacuo to give a brown oil (39 g). Analytical chiral HPLC on Chiralpak AD-H column (250 mm x4.6 mm) eluting isocratically with 20% EtOH (containing 0.2% isopropylamine) - heptane, flow rate = 1.0 mL/min, detecting at 215 nm indicated the oil was a mixture of two diastereoisomers : Peak 1 RT = 7.87 min, 90.4 %; Peak 2 RT = 9.78 min, 9.6 %. The mixture was separated by chiral preparative HPLC on a Chiralpak AD column (50 mm x 200 mm), eluting with 20% ethanol (containing 0.2% isopropylamine)-heptanes, flow rate=50 mL/min, detecting at 240 nm, collecting fractions of the major component with RT = 11-16 min. The combined fractions were evaporated under reduced pressure to give the major isomer of the title compound (isomer 1) (25.1 g, 45%) as a brown oil: LCMS (System A) RT= 1.25 min, ES+ve m/z 540 (M+H)+; Analytical chiral HPLC on Chiralpak AD-H column RT = 7.87 min, >99.5%; H NMR δ (CDCI3; 600 MHz) 9.07 (dd, 7=4.2, 2.0 Hz, 1H), 8.15 (dd, 7=8.0, 1.9 Hz, 1H), 8.08 (d, 7=8.4 Hz, 1H), 7.43 (dd, 7=8.0, 4.3 Hz, 1H), 7.37 (d, 7=8.3 Hz, 1H), 7.37 - 7.33 (m, 1H), 7.27 (d, 7=1.1 Hz, 1H), 7.27 - 7.25 (m, 1H), 7.21 (d, 7=7.7 Hz, 1H), 5.98 (s, 1H), 3.31 (d, 7=5.3 Hz, 1H), 3.10 - 2.95 (m, 2H), 2.85 (dd, 7=15.4, 5.7 Hz, 1H), 2.84 - 2.79 (m, 1H), 2.78 - 2.71 (m, 1H), 2.75 - 2.67 (m, 1H), 2.55 - 2.47 (m, 1H), 2.48 - 2.41 (m, 1H), 2.43 - 2.35 (m, 1H), 2.30 (s, 3H), 2.27 (s, 3H), 2.26 - 2.18 (m, 1H), 2.23 - 2.13 (m, 1H), 2.02 - 1.95 (m, 1H), 1.98 - 1.91 (m, 2H), 1.50 - 1.42 (m, 1H), 1.30 (s, 9H). The fractions containing the minor component (RT= 19-25 min) were combined and concentrated under reduced pressure to give the title compound isomer 2 (2.03g, 4%) as a brown oil: LCMS (System A) RT= 1.25 min, ES+ve m/z 540 (M+H)+; Analytical chiral HPLC on Chiralpak AD-H column RT=9.78 min, >99.5%.
1: 45% 2: 4%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; R-(+)-1,1'-binaphthyl-2,2'-diphenylphosphine; potassium hydroxide In 1,4-dioxane at 90℃; for 1h; Inert atmosphere;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1 Location in patent: Page/Page column 34; 35
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

25
[ 1025735-46-9 ]
[ 1629249-78-0 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide In water; toluene at 75 - 85℃; for 5h; Inert atmosphere; Large scale; Overall yield = 51%; Overall yield = 49.4 kg; Optical yield = 80 %de;	48 methyl 4-((R)-3-(2-(1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)-3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)butanoate Stage 6. To a reactor was charged toluene (25 kg), (A^-methyl 4-(3-(2-(l,8-naphthyridin-2- yl)ethyl)pyrrolidin-l-yl)but-2-enoate (Intermediate 47 in toluene (42.15 kg, 13.4% assay, 5.6 kg (lwt) active), 17%w/w aq. KOH solution (10 kg), (3-(3,5-dimethyl-l pyrazol-l-yl)phenyl)boronic acid (Intermediate 9) (8.4 kg), chloro-(l,5-cyclooctadiene)rhodium (I) dimer (0.433 kg) and (R)- (+)-2,2'-bis(diphenylphosphino)-l,l'-binaphthyl (1.3 kg). The reactor was purged with nitrogen, heated to 75-85°C and stirred under nitrogen for about 5 h. The mixture was distilled under reduced pressure to l-3vol and cooled to 20-30°C. The mixture was treated with DCM (166 kg) and water (57 kg), stirred and the aqueous phase discarded. The organic phase was acidified with 0.5N aq. HCI solution (141 kg), separated and the aqueous phase washed twice with DCM (45 and 43 kg). Ethyl acetate (57 kg) was added into the aqueous phase and the mixture neutralised to pH7-8 with IN aq. NaOH (56 kg). The organic layer was collected and the aqueous layer was extracted twice with ethyl acetate (2x28 kg). The combined EtOAc extracts were washed with 25% aq. NaCI (32 kg) and distilled under reduced pressure to l-2vol. The mixture was diluted with MeOH (25 kg) and distilled under reduced pressure to l-2vol. The residue was diluted with MeOH (29 kg) to give a solution of the title compounds MeOH (~9: ldr, 49.4 kg, 9.0%assay, 51%th yield). HPLC RT = 11.68 min, 90.9%, Column: 150 mm χ 4.6 mm ID, 3.5 μηη Agilent Zorbax SB-C8 Flow Rate: 1.0 mL/min. Temp.: 40°C Detection wavelength: 210 nm Solvents: A: 0.05% v/v solution of trifluoroacetic acid in water B: 0.05% v/v solution of trifluoroacetic acid in acetonitrile Gradient: Time (min) A% B% 0.0 95 5 15.0 30 70 18.0 5 95 20.0 5 95 20.1 95 5 Chiral HPLC RT = 10.27 min, 90.0%, Column: 250 mm χ 4.6 mm ID, 5 μηη CHIRALPAK AD-H Flow Rate: 1.0 mL/min. Temp.: 40°C Detection wavelength: 248 nm Solvents: A: 0.1% v/v solution of diethyl amine in n-hexane B: 0.1% v/v solution of diethylamine in ethanol Gradient: Time (min) A% B% 0.01 80 20 40 80 20

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/154725, 2014, A1 Location in patent: Page/Page column 52; 53

26
[ 294877-29-5 ]
(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)boronic acid [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5992 - 6009

27
[ 1025735-46-9 ]
[ 1629249-93-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C

Reference： [1]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

28
[ 1025735-46-9 ]
[ 1629249-94-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C

Reference： [1]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

29
[ 1025735-46-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 4.2: 2.5 h / -78 - 20 °C 5.1: HPLC on a Chiralcel OD-Hcolumn / Resolution of racemate 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 16 h / 4 °C 7.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 7.2: 2 h / 20 °C 8.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 96 h 9.1: trifluoroacetic acid / chloroform / 2 h / 20 °C 10.1: borane-THF / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 10.2: 20 °C / Inert atmosphere
	Multi-step reaction with 9 steps 1.1: dichlorobis(tri-O-tolylphosphine)palladium; potassium phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 1.2: 6 h / Reflux 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C 4.2: 48 h / -78 - 20 °C 5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran / 2 h / 4 °C 6.1: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h 6.2: 2 h / 20 °C 7.1: hydrogen; 5% rhodium-on-charcoal / ethanol / 96 h 8.1: trifluoroacetic acid / chloroform / 2 h / 20 °C 9.1: borane-THF / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 9.2: 20 °C / Inert atmosphere

Reference： [1]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]
[2]Anderson, Niall A.; Campbell, Ian B.; Fallon, Brendan J.; Lynn, Sean M.; Macdonald, Simon J. F.; Pritchard, John M.; Procopiou, Panayiotis A.; Sollis, Steven L.; Thorp, Lee R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5992 - 6009]

30
[ 1025735-46-9 ]
[ 1888440-91-2 ]
[ 2365406-22-8 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide In 1,4-dioxane; water at 90℃; Inert atmosphere; diastereoselective reaction;

Reference： [1]Procopiou, Panayiotis A.; Anderson, Niall A.; Barrett, John; Barrett, Tim N.; Crawford, Matthew H. J.; Fallon, Brendan J.; Hancock, Ashley P.; Le, Joelle; Lemma, Seble; Marshall, Richard P.; Morrell, Josie; Pritchard, John M.; Rowedder, James E.; Saklatvala, Paula; Slack, Robert J.; Sollis, Steven L.; Suckling, Colin J.; Thorp, Lee R.; Vitulli, Giovanni; Macdonald, Simon J. F. [Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8417 - 8443]

31
[ 1025735-46-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; caesium carbonate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine / toluene / 18 h / 100 °C 2: potassium carbonate; water / methanol / 5 h / 20 °C 3: acetonitrile / 0.17 h / 50 °C

Reference： [1]Sap, Jeroen B. I.; Wilson, Thomas C.; Kee, Choon Wee; Straathof, Natan J.W.; Ende, Christopher W.am; Mukherjee, Paramita; Zhang, Lei; Genicot, Christophe; Gouverneur, Véronique [Chemical Science, 2019, vol. 10, # 11, p. 3237 - 3241]

32
[ 1025735-46-9 ]
[ 2284517-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(l) iodide; caesium carbonate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine / toluene / 18 h / 100 °C 2: potassium carbonate; water / methanol / 5 h / 20 °C

Reference： [1]Sap, Jeroen B. I.; Wilson, Thomas C.; Kee, Choon Wee; Straathof, Natan J.W.; Ende, Christopher W.am; Mukherjee, Paramita; Zhang, Lei; Genicot, Christophe; Gouverneur, Véronique [Chemical Science, 2019, vol. 10, # 11, p. 3237 - 3241]

33
[ 1025735-46-9 ]
[ 2284518-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: copper(l) iodide; caesium carbonate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine / toluene / 18 h / 100 °C 2: potassium carbonate; water / methanol / 5 h / 20 °C 3: acetonitrile / 0.17 h / 50 °C 4: (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; tetraethylammonium (F<SUP>18</SUP>)-flouride / N,N-dimethyl-formamide / 0.33 h / 50 °C

Reference： [1]Sap, Jeroen B. I.; Wilson, Thomas C.; Kee, Choon Wee; Straathof, Natan J.W.; Ende, Christopher W.am; Mukherjee, Paramita; Zhang, Lei; Genicot, Christophe; Gouverneur, Véronique [Chemical Science, 2019, vol. 10, # 11, p. 3237 - 3241]

34
[ 401-55-8 ]
[ 1025735-46-9 ]
[ 2284517-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; caesium carbonate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In toluene at 100℃; for 18h;

Reference： [1]Sap, Jeroen B. I.; Wilson, Thomas C.; Kee, Choon Wee; Straathof, Natan J.W.; Ende, Christopher W.am; Mukherjee, Paramita; Zhang, Lei; Genicot, Christophe; Gouverneur, Véronique [Chemical Science, 2019, vol. 10, # 11, p. 3237 - 3241]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1025735-46-9	MDL No. :	MFCD08572151
Formula :	C₁₁H₁₃BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RBSKBRQNRWKHSP-UHFFFAOYSA-N
M.W :	216.04 g/mol	Pubchem ID :	16640550
Synonyms :

Num. heavy atoms :	16
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.18
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	63.32
TPSA :	58.28 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	0.17
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	-0.19
Consensus Log Po/w :	0.43

[ CAS No. 1025735-46-9 ]

Quality Control of [ 1025735-46-9 ]

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Product Details of [ 1025735-46-9 ]

Calculated chemistry of [ 1025735-46-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1025735-46-9 ]

Application In Synthesis of [ 1025735-46-9 ]

[ 1025735-46-9 ] Synthesis Path-Downstream 1~34

Related Functional Groups of
[ 1025735-46-9 ]

Organoboron

Aryls

Related Parent Nucleus of
[ 1025735-46-9 ]

Pyrazoles

Precautionary Statements-General

Prevention

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Physical hazards

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Inquiry

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

Log S (ESOL) :	-2.56
Solubility :	0.589 mg/ml ; 0.00273 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.793 mg/ml ; 0.00367 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.6
Solubility :	0.543 mg/ml ; 0.00251 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.29

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1025735-46-9 ]

Quality Control of [ 1025735-46-9 ]

Related Doc. of [ 1025735-46-9 ]

Product Details of [ 1025735-46-9 ]

Calculated chemistry of [ 1025735-46-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1025735-46-9 ]

Application In Synthesis of [ 1025735-46-9 ]

[ 1025735-46-9 ] Synthesis Path-Downstream 1~34

Related Functional Groups of [ 1025735-46-9 ]

Organoboron

Aryls

Related Parent Nucleus of [ 1025735-46-9 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1025735-46-9 ]

Related Parent Nucleus of
[ 1025735-46-9 ]