[ CAS No. 73852-17-2 ] {[proInfo.proName]}

Name: 73852-17-2|(2,6-Dichlorophenyl)boronic acid|97%
Brand: Ambeed
SKU: A175557
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Quality Control of [ 73852-17-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 73852-17-2 ]

Product Details of [ 73852-17-2 ]

CAS No. :	73852-17-2	MDL No. :	MFCD00064869
Formula :	C₆H₅BCl₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CXDPUSMFYPQXCV-UHFFFAOYSA-N
M.W :	190.82	Pubchem ID :	2734332
Synonyms :

Calculated chemistry of [ 73852-17-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.29
TPSA :	40.46 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) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.08
Log Po/w (WLOGP) :	0.67
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	0.57
Consensus Log Po/w :	0.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.67
Solubility :	0.407 mg/ml ; 0.00213 mol/l
Class :	Soluble
Log S (Ali) :	-2.56
Solubility :	0.526 mg/ml ; 0.00276 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.52
Solubility :	0.572 mg/ml ; 0.003 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.01

Safety of [ 73852-17-2 ]

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

Application In Synthesis of [ 73852-17-2 ]

* 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 [ 73852-17-2 ]
Downstream synthetic route of [ 73852-17-2 ]

[ 73852-17-2 ] Synthesis Path-Upstream 1~3

1
[ 688-74-4 ]
[ 541-73-1 ]
[ 73852-17-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: at -80 - -50℃; for 2 h; Inert atmosphere Stage #2: Inert atmosphere	(1) Lithiation: under the protection of nitrogen,First in a 1000mL three-necked flask,Add 50g of 1,3-dichlorobenzene and cool to -80~-60°C.Then add 176 mL of n-butyl lithium dropwise.The dropping process is maintained at -80 to -50 ° C.After the completion of the dropwise addition, the reaction was kept for 2 hours.(2) Lithium-hydrogen exchange:117 g of tributyl borate liquid was added dropwise to the solution of the above-obtained phenyl lithium,After the addition is completed, the heat retention reaction is carried out.After the reaction, the reaction system was stirred by adding hydrochloric acid having a mass concentration of 10percent.Then let go of the layering,Extracted,Combine the organic layers,Desolvent,Hydrating succinol to obtain 51.7 g of crude 4-phenoxybenzeneboronic acid in a yield of 80percent;(3) Purification:51.7 g of crude 4-phenoxyphenylboronic acid was added to a 1 L three-necked flask.Add 200 mL of methyl tert-butyl ether to dissolve,Desolvent,Cooling, crystallization, and centrifugation gave 48.4 g of 4-phenoxybenzeneboronic acid product in a yield of 75percent.

Reference： [1] Patent: CN108084217, 2018, A, . Location in patent: Paragraph 0006; 0017-0020; 0022-0024; 0026-0028; 0030-0032

2
[ 19393-92-1 ]
[ 73852-17-2 ]

Reference： [1] Patent: US6521666, 2003, B1,

3
[ 541-73-1 ]
[ 73852-17-2 ]

Reference： [1] ACS Catalysis, 2015, vol. 5, # 9, p. 5366 - 5372

[ 73852-17-2 ] Synthesis Path-Downstream 1~88

1
[ 904283-16-5 ]
[ 73852-17-2 ]
<i>N</i>-(3-chloro-4-fluoro-phenyl)-2-[1-cyclopentyl-4-(2',6'-dichloro-biphenyl-4-yl)-piperidin-4-ylamino]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3668 - 3673

2
[ 500889-65-6 ]
[ 73852-17-2 ]
[ 929194-33-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 602 - 608

3
[ 867330-26-5 ]
[ 73852-17-2 ]
[ 867333-31-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 602 - 608
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5812 - 5818
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 1546 - 1559

4
[ 623144-17-2 ]
[ 73852-17-2 ]
[ 623144-23-0 ]

Yield	Reaction Conditions	Operation in experiment
62%		To a solution of 3g of 6- (benzyloxy)-2-chloroquinoline 12 in toluene (294ml) is added Pd (PPh3) 4 (1 g). After 30 minutes, a solution of <strong>[73852-17-2]2, 6-dichlorophenylboronic acid</strong> (4.22 g) in methanol (186 ml) and 120 ml of a saturated aqueous solution of NaHC03 is added. The reaction is heated under reflux for 4h. After evaporation, the aqueous phase is extracted with AcOEt (3x20ml). The organic phases are washed with brine, dried over MgS04 and evaporated to dryness. The residue is purified over silica gel using AcOEt/petroleum ether 5/95 then 10/90 as eluent to give 6- (benzyloxy)-2- (2, 6- dichlorophenyl) quinoline 19 as an oil. Yield: 62 %. MS (MH+): 380.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 142 - 146
[2]Patent: WO2003/93237,2003,A1 .Location in patent: Page/Page column 57

5
[ 852116-38-2 ]
[ 73852-17-2 ]
[ 852122-56-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 302 (+-)-[7-(2,6-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}amine The title compound was prepared (0.030 g, 21%) following the general procedure of Example 154 as a white solid, hydrochloride salt from (+-)-(7-bromo-5-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.56 g, 1.41 mmol) and 2,6 dichlorophenylboronic acid (2.17 g, 14.10 mmol). mp 193-195 C.

Reference： [1]Patent: US2005/261347,2005,A1

6
[ 73852-17-2 ]
(2-bromo-4-isopropyl-phenyl)-[4-(2,6-dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1057 - 1062

7
[ 73852-17-2 ]
(2-bromo-4-isopropyl-phenyl)-[4-(2,6-dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-ethyl-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1057 - 1062

8
[ 893392-78-4 ]
[ 73852-17-2 ]
[ 893394-35-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With cesium fluoride;bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; at 100℃;	Scheme C4; [00309] A reaction flask was charged, under N2, with C24 (74 mg, 0.19 mmol),<strong>[73852-17-2]2,6-dichlorophenylboronic acid</strong> (57 mg, 0.30 mmol), CsF (35 mg, 0.23 mmol), Pd(tBu3P)2 (5 mol%), and dioxane (2 mL). The reaction was heated at 100C overnight. The crude reaction mixture was purified by silica gel chromatography eluting with 2% Et2O in hexanes. Isolated 54mg, 54% yield, of C14 as a light yellow solid. 1H NMR (300 MHz, CDCl3) delta 1.39 (s, 9H, 'Bu), 7.24-7.45 (m, 8H), 7.62-7.67 (m, 3H), 12.41 (s, 1H, OH). EPO <DP n="78"/>[00310] Ligands C18, C22, and C23 were synthesized as described for C14 in yields of 25%, 50%, and 37%, respectively.[00311] Ligands C17 and C19 were synthesized as described for C14 but usingPd(PPh3) 4, Na2CO3, and toluene. Yield of C17 was 60% and C19 was 54%.

Reference： [1]Patent: WO2006/66126,2006,A2 .Location in patent: Page/Page column 75-76

9
[ 328918-33-8 ]
[ 73852-17-2 ]
[ 247940-06-3 ]
[ 328918-90-7 ]
[ 328919-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride;palladium diacetate; In tetrahydrofuran;	A. 2-(4-{2-[2-(2',6'-Dichloro-biphenyl-4-yl)-5-methyloxazol-4-yl]-ethoxy}-phenoxy)-2-methylpropionic acid ethyl ester A solution of 2-(4-{2-[2-(4-bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic acid ethyl ester (300 mg, 0.614 mmol) (see Ex. 2, part B), 2,6-dichlorophenylboronic acid (0.921 mmol), potassium fluoride (88.6 mg, 1.84 mmol), palladium acetate (1.3 mg, 0.14 mumol), and 2-(dicyclohexylphosphino)biphenyl (4.3 mg, 12.3 mumol) were combined under N2, to which anhydrous THF (1.23 mL) was added. The yellow mixture was heated at reflux for 12 h. After cooling to room temperature, the mixture was partitioned between Et2O (20 mL) and 1M NaOH (10 mL). The layers were separated, and the aqueous phase was back-extracted with Et2O (10 mL). Combined organic phases were dried over Na2SO4, and concentrated. The product was purified by silica gel chromatography (25 g SiO2, 1:4 ethyl acetate:hexanes) to yield the desired product as an oil. Rf=0.50 in 1:4 ethyl acetate:hexanes; MS (EI) 554.2 (M+H)+.

Reference： [1]Patent: US6417212,2002,B1

10
Pd(dppf)2Cl₂ [ No CAS ]
[ 313688-72-1 ]
[ 73852-17-2 ]
[ 313671-44-2 ]

Yield	Reaction Conditions	Operation in experiment
26%	With triethanolamine; In 1,2-dimethoxyethane; hexane; ethyl acetate;	Step A A mixture of tert-butyl (8aS,12aR)-2-bromo-4,5,6,7,9,10,12,12a-octahydroazepino[3,2,1-hi]pyrido[4,3-b]indole-11(8aH)-carboxylate (0.10 g, 0.25 mmol), <strong>[73852-17-2]2,6-dichlorophenylboronic acid</strong> (0.10 g, 0.50 mmol), Pd(dppf)2Cl2 (10 mg, 0.012 mmol) and TEA (1.0 mL, 7.2 mmol) in DME (15 mL) was degassed at 40-50 C. and refluxed for 32 h. The mixture was concentrated in vacuo and EtOAc (20 mL) was added. The solution was washed with saturated Na2CO3 (2*10 mL), dried (Na2SO4) and concentrated in vacuo. Normal phase HPLC (5% EtOAc in hexane) gave tert-butyl (8aS,12aR)-2-(2,6-dichlorophenyl)-4,5,6,7,8a,9,10,11,12,12a-decahydroazepino[3,2,1-hi]pyrido[4,3-b]indole-11(8aH)-carboxylate (0.030 g, 26%) as a white foam. MS (ESI): 473 (base, M+H).
26%	With triethanolamine; In 1,2-dimethoxyethane; hexane; ethyl acetate;	Step A A mixture of tert-butyl (8aS,12aR)-2-bromo-4,5,6,7,9,10,12,12a-octahydroazepino[3,2,1-hi]pyrido[4,3-b]indole-11(8aH)-carboxylate (0.10 g, 0.25 mmol), <strong>[73852-17-2]2,6-dichlorophenylboronic acid</strong> (0.10 g, 0.50 mmol), Pd(dppf)2Cl2 (10 mg, 0.012 mmol) and TEA (1.0 mL, 7.2 mmol) in DME (15 mL) was degassed at 40-50 C. and refluxed for 32 h. The mixture was concentrated in vacuo and EtOAc (20 mL) was added. The solution was washed with saturated Na2CO3 (2*10 mL), dried (Na2SO4) and concentrated in vacuo. Normal phase HPLC (5% EtOAc in hexane) gave tert-butyl (8aS,12aR)-2-(2,6-dichlorophenyl)-4,5,6,7,8a,9,10,11,12,12a-decahydroazepino[3,2,1-hi]pyrido[4,3-b]indole-11(8aH)-carboxylate (0.030 g, 26%) as a white foam. MS (ESI): 473 (base, M+H).

Reference： [1]Patent: US6548493,2003,B1
[2]Patent: US2004/209864,2004,A1

11
tert-butyl (6AS,10AR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6AH)-carboxylate [ No CAS ]
[ 73852-17-2 ]
[ 313668-81-4 ]

Yield	Reaction Conditions	Operation in experiment
		(6aS,10aR)-2-(2,6-dichlorophenyl)-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole The title compound was prepared by Example 305, Step A, from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate and the corresponding <strong>[73852-17-2]2,6-dichlorobenzeneboronic acid</strong> followed by hydrolysis of the resultant BOC protected amine adduct by the procedure of Example 305, Step B. 1H NMR (CDCl3, 300 MHz) delta7.38 (dd, 2H), 7.15 (t, 1H), 6.80 (d, 1H), 6.73 (d, 1H), 3.69 (td, 1H), 3.57-3.30(m, 3H), 3.28-3.00 (m, 3H), 3.00-2.83 (m, 3H), 2.20 (bs, 2H), 2.00-1.81 (m, 2H). MS (CI): 346 (M+H+).

Reference： [1]Patent: US6548493,2003,B1

12
(MeO)3B [ No CAS ]
[ 19393-92-1 ]
[ 73852-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; water;	Reference Example 1 2,6-Dichlorobenzeneboronic acid <strong>[19393-92-1]1-Bromo-2,6-dichlorobenzene</strong> (2.00 g) was dissolved in freshly distilled THF (7 mL). This solution was cooled to -78° C. and n-BuLi (8.3 mL of a 1.6M solution in hexane) was added dropwise to the cold solution under N2. The mixture was stirred for 5 min at -78° C. and (MeO)3B (2.2 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight. Water was added and the resulting mixture was stirred for 0.5 h, then acidified with HOAc and extracted with EtOAc. The organic layer was further washed with water and brine, dried (MgSO4) filtered and evaporated to yield 2,6-dichlorobenzeneboronic acid (1.6 g)

Reference： [1]Patent: US6521666,2003,B1

13
[ 947410-34-6 ]
[ 73852-17-2 ]
[3-amino-2-(2,6-dichlorophenyl)pyridin-4-yl](phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium carbonate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 100℃; for 48h;	In a Schlenk tube were charged the compound of Preparation 1 (100 mg, 0.36 mmol), 2,6- dichlorophenyl boronic acid (137 mg, 0.72 mmol), potassium carbonate (229 mg, 1.08 mmol) and toluene (3 ml_). The mixture was submitted to three vacuum-argon cycles, then S-PHOS (9 mg, 0.022 mmol) and tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.011 mmol) was added and the mixture purged in the same way. The reaction was stirred at 1000C under argon for 2 days. Subsequently, water was added to the cold reaction mixture and it was extracted with ethyl acetate (3 x 50 ml), the organic solution was washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica flash, using hexane/ethyl acetate (6/1 ) as eluents, to yield the title compound (44 mg, 36%) as a yellow solid.LRMS (m/z): 343, 345, 347 (M+1)+. Retention Time: 15 min.H1-NMR delta (CDCI3): 5.73 (brs, 2H), 7.25-7.8 (m, 9H), 8.13 (d, J=5.3 Hz, 1 H).

Reference： [1]Patent: WO2007/96072,2007,A2 .Location in patent: Page/Page column 56

14
tert-butyl (6AS,10AR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6AH)-carboxylate [ No CAS ]
[ 313667-20-8 ]
[ 73852-17-2 ]
[ 313668-81-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 306 (6aS,10aR)-2-(2,6-dichlorophenyl)-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole The title compound was prepared by Example 305, Step A, from tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate and the corresponding <strong>[73852-17-2]2,6-dichlorobenzeneboronic acid</strong> followed by hydrolysis of the resultant BOC protected amine adduct by the procedure of Example 305, Step B. 1H NMR (CDCl3, 300 MHz) delta 7.38 (dd, 2H), 7.15 (t, 1H), 6.80 (d, 1H), 6.73 (d, 1H), 3.69 (td, 1H), 3.57-3.30(m, 3H), 3.28-3.00 (m, 3H), 3.00-2.83 (m, 3H), 2.20 (bs, 2H), 2.00-1.81 (m, 2H). MS (CI): 346 (M+H+).

Reference： [1]Patent: US2004/209864,2004,A1

15
[ 947410-60-8 ]
[ 73852-17-2 ]
[3-amino-2-(2,6-dichlorophenyl)pyridin-4-yl](2-chloro-4-fluorophenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); at 110℃; for 72h;	In a Schlenk tube were charged the compound of Preparation 4e (7.33 g, 22.24 mmol), <strong>[73852-17-2]2,6-dichlorophenyl boronic acid</strong> (8.6 g, 45.07 mmol), potassium phosphate (14.2 g, 66.9 mmol) and toluene (140 ml_). The mixture was submitted to three vacuum-argon cycles, then 2-(dicyclohexylphosphino)26'-dimethoxy-1-1Ibiphenyl (S-PHOS) (0.92 g, 2.24 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.24 g, 1.35 mmol) were added and the mixture purged in the same way. The reaction was stirred at 1100C under argon for 3 days. Subsequently, the cold reaction mixture was filterd through Celite and washed with more toluene (60 ml_). The residue was directly purified by column chromatography on silica gel, using hexane/diethyl ether (9:1 to 2:8) as eluent, to yield the title compound (3.01 g, 34%) as a yellow solid.LRMS (m/z): 395, 397, 399, 401 (M+1)+.1H-NMR delta (CDCI3): 6.16 (brs, 2H), 7.07 (d, J=6 Hz, 1 H), 7.11-7.18 (m, 1 H), 7.25-7.29 (m, 1 H), 7.35-7.45 (m, 2H), 7.48-7.52 (m, 2H), 8.04 (d, J=6 Hz, 1 H).

Reference： [1]Patent: WO2008/131922,2008,A1 .Location in patent: Page/Page column 56-57

16
[ 1149379-07-6 ]
[ 73852-17-2 ]
[ 1149379-08-7 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride; tri tert-butylphosphoniumtetrafluoroborate;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 70℃; for 16h;	To a two-neck round bottom flask with a magnetic stirring bar, was added tris(dibenzylideneacetone)dipalladium(0) (29.5 mg, 0.032 mmol), tri-t-butylphosphonium tetrafluoroborate (18.6 mg, 0.064 mmol), cesium fluoride (652 g, 4.29 mmol), 2,6- dichlorophenylboronic acid (409 mg, 2.15 mmol), and the product of Step E (500 mg, 1.07 mmol). One neck of the flask was connected to a vacuum line while another neck was fitted with an argon balloon. The flask was then purged 8-10 times with argon. The vacuum line was replaced with a septum and anhydrous THF (1O mL) was added by syringe. The mixture was stirred in a 70C oil bath for 16 h. The reaction solution was filtrated and concentrated. The residue was carried on to hydrolysis at the next step without purification.

Reference： [1]Patent: WO2009/58237,2009,A1 .Location in patent: Page/Page column 31

17
[ 108-90-7 ]
[ 73852-17-2 ]
[ 33146-45-1 ]

Reference： [1]RSC Advances,2017,vol. 7,p. 47104 - 47110
[2]Journal of the American Chemical Society,2009,vol. 131,p. 2060 - 2061

18
[ 51437-00-4 ]
[ 73852-17-2 ]
[ 851534-94-6 ]

Yield	Reaction Conditions	Operation in experiment
		1.1 g of tetrakistriphenylphosphine palladium was added at room temperature to a solution having 9.5 g of 5-bromo-2-fluorotoluene dissolved in 150 ml of toluene, followed by stirring for 10 minutes. 13.4 g of 2,6- dichlorophenyl boronic acid, 30 ml of ethanol, 50 ml of a 2M sodium carbonate aqueous solution and 10.6 g of sodium carbonate powder were added thereto, and the reaction system was flushed with nitrogen, followed by stirring for 15 hours under reflux under heating. After cooling, the reaction solution was filtered through celite, and the filtrate was dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel (Silica gel 60N; spherical and neutral, manufactured by Kanto Kagaku) column chromatography (developing solvent: n- hexane only) to obtain 6.5 g of 5- (2', 6'-dichlorophenyl)- 2-fluorotoluene as an oily substrate. Further, NMR of this compound was as follows. H-NMR 5 (ppm) 2.34 (d, 3H; J =2. 1 Hz), 7. 05-7. 13 (m, 3H), 7.21 (t, lH; J =7.5 Hz), 7.39 (d, 2H; J =7. 5 Hz)

Reference： [1]Patent: WO2005/44007,2005,A1 .Location in patent: Page/Page column 51-52

19
[ 38762-41-3 ]
[ 73852-17-2 ]
[ 1148126-10-6 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2683 - 2693

20
[ 104-92-7 ]
[ 73852-17-2 ]
[ 1172623-10-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2452 - 2457

21
[ 99-90-1 ]
[ 73852-17-2 ]
[ 50987-27-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2452 - 2457

22
[ 947410-36-8 ]
[ 73852-17-2 ]
[3-amino-2-(2,6-dichlorophenyl)pyridin-4-yl](2,4-difluorophenyl)-methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5531 - 5545

23
[ 1206181-57-8 ]
[ 73852-17-2 ]
[ 1206181-68-1 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 102 - 110

24
[ 881658-92-0 ]
[ 73852-17-2 ]
[ 1217296-48-4 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1352 - 1355

25
[ 657408-07-6 ]
potassium phosphate [ No CAS ]
3-bromo-6,7-dimethylmidazo[1,2-f]phenanthridine [ No CAS ]
[ 73852-17-2 ]
[ 946147-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	tris-(dibenzylideneacetone)dipalladium(0); In toluene;	Step 1 To a 500 mL round flask was added 3-bromo-6,7-dimethylmidazo[1,2-f]phenanthridine (8.2 g, 25.2 mmol), 2,6-dichlorophenylboronic acid (19.2 g, 100.9 mmol), Pd2(dba)3 (2.29 g, 2.5 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 4.11 g, 10.0 mmol), potassium phosphate tribasic (26.7 g, 126 mmol), and 250 mL of toluene. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 48 hours. After cooling, the mixture was purified by a silica gel column. Yield of 3-(2,6-dichlorophenyl)-6,7-dimethylimidazo[1,2-f]phenanthridine was 2.4 g.

Reference： [1]Patent: EP2243785,2010,A1

26
6-chloro-4-ethoxy-pteridin-2-ylamine [ No CAS ]
[ 73852-17-2 ]
[ 1003843-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In Dimethyl ether; water; at 100℃; for 0.166667h;Microwave irradiation;	Examples 1 to 73 Synthesis of 2-amino-4-ethoxy-6-substituted pteridinesThe synthetic method may be represented schematically as follows: The general procedure used for preparing 2-amino-6-aryl-4-ethoxy-pteridines and 2-amino-6-heteroaryl-4-ethoxy-pteridines starts from the common intermediate 2-amino-6-chloro-4-ethoxypteridine (described in WO 2005/025574) as follows. A mixture of 2-amino-6-chloro-4-ethoxypteridine (23 mg, 0.1 mmol), potassium carbonate (27 mg, 0.2 mmol), tetrakis(triphenylphosphine) palladium (8 mg, 0.007 mmol) and a suitable arylboronic or heteroarylboronic acid, or a pinacol ester thereof, (0.12 mmol) in dimethylether (1.5 mL) and water (1 mL) was heated to 100 C. for 10 minutes under microwave irradiation. Solvents were concentrated in vacuo and the residue was purified by high performance liquid chromatography (hereinafter referred as HPLC) onto a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, in order to afford the pure desired product. This procedure provided, with yield ranging from 5% to 65%, depending upon the aryl or heteroaryl group R introduced at position 6 of the pteridine ring, the pure compounds shown in the table 1, which were characterized by their mass spectrum MS.

Reference： [1]Patent: US2010/305117,2010,A1 .Location in patent: Page/Page column 15

27
[ 73852-17-2 ]
[ 376584-36-0 ]
[ 1271523-25-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; silver carbonate; In tetrahydrofuran; for 1h;Reflux;	A suspension of (6) (2.50g, 5.8mmol), <strong>[73852-17-2]2,6-dichlorophenylboronic acid</strong> (1.66g, 8.7mmol), tetrakis(triphenylphosphine)palladium(0) (3.36g, 2.9mmol), K2C03 (1.60g, 11.6mmol) and Ag2C03 (8.00g, 29mmol) in THF (100ml) was heated at reflux for lhr. The inorganics were removed by filtration and the filtrated reduced onto silica. Column chromatography (Si02; 4: 1?1 :1 PE:EtOAc) gave the title compound; (1.40g, 2.6mmol)NMR delta 7.93 (IH, d, J 8.8), 7.63-7.79 (3H, m), 7.40-7.52 (2H, m), 7.17-7.32 (3H, m), 7.08 (IH, d, J 8.2), 6.84 (2H, d, J 8.2), 5.24 (IH, d, J 8.2), 5.18 (2H, s), 3.72 (3H, s), 1.41 (9H, s);MS (m/e) 540 [MH]+, Rt 2.86min (QC Method 3)

Reference： [1]Patent: WO2011/27156,2011,A1 .Location in patent: Page/Page column 42-43

28
[ 1319741-16-6 ]
[ 73852-17-2 ]
[ 1095716-17-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2832 - 2835

29
[ 174669-74-0 ]
[ 73852-17-2 ]
[ 1339958-98-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4146 - 4149

30
[ 73852-17-2 ]
[ 1318800-59-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4146 - 4149

31
[ 73852-17-2 ]
[ 1318800-64-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4146 - 4149

32
[ 73852-17-2 ]
[ 1318800-54-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4146 - 4149

33
[ 92-66-0 ]
[ 73852-17-2 ]
[ 61576-84-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 40h;Inert atmosphere;	General procedure: To a 20 mL sealable tube was added sequentially the aryl halide (0.53 mmol), the aryl or heteroaryl pinacolboronate or boronic acid (1.06 mmol, 2.0 equiv.), copper(I) chloride (52.5 mg, 0.106 mmol, 1.00 equiv.), palladium(II) acetate (5.95 mg, 0.027 mmol, 5 mol%), S-Phos or X-Phos (0.106 mmol, 20 mol%), and cesium carbonate (691 mg, 2.12 mmol, 4.00 equiv.). DMF (5.3 mL, 0.1 M) was added, the vial flushed quickly with Ar, and sealed. The reaction mixture was warmed to 100 C and stirred vigorously for 2 h or the appropriate time (the standard reaction time was 2 h, but if the reaction was not complete at this time, the reaction was continued for 16 h; the reaction was stopped if no further conversion was seen. In addition, some reactions were judged to be complete in less than 2 h, some between 15-30 min). The reaction mixture was cooled to ambient temperature and quenched with saturated aqueous ammonium chloride (10 mL). The aqueous phase was extracted with ethyl acetate (3 x 15 mL). The combined organic phases were washed with saturated aqueous ammonium chloride (2 x 10 mL) and brine (1 x 10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with ethyl acetate-hexanes or methanol-methylene chloride to afford the product. Reactions without copper were performed exactly as described above except for omission of copper (I) chloride.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5055 - 5059

34
[ 2051-62-9 ]
[ 73852-17-2 ]
[ 61576-84-9 ]

Yield	Reaction Conditions	Operation in experiment
12%Chromat.	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	General procedure: To a 20 mL sealable tube was added sequentially the aryl halide (0.53 mmol), the aryl or heteroaryl pinacolboronate or boronic acid (1.06 mmol, 2.0 equiv.), copper(I) chloride (52.5 mg, 0.106 mmol, 1.00 equiv.), palladium(II) acetate (5.95 mg, 0.027 mmol, 5 mol%), S-Phos or X-Phos (0.106 mmol, 20 mol%), and cesium carbonate (691 mg, 2.12 mmol, 4.00 equiv.). DMF (5.3 mL, 0.1 M) was added, the vial flushed quickly with Ar, and sealed. The reaction mixture was warmed to 100 C and stirred vigorously for 2 h or the appropriate time (the standard reaction time was 2 h, but if the reaction was not complete at this time, the reaction was continued for 16 h; the reaction was stopped if no further conversion was seen. In addition, some reactions were judged to be complete in less than 2 h, some between 15-30 min). The reaction mixture was cooled to ambient temperature and quenched with saturated aqueous ammonium chloride (10 mL). The aqueous phase was extracted with ethyl acetate (3 x 15 mL). The combined organic phases were washed with saturated aqueous ammonium chloride (2 x 10 mL) and brine (1 x 10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with ethyl acetate-hexanes or methanol-methylene chloride to afford the product. Reactions without copper were performed exactly as described above except for omission of copper (I) chloride.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5055 - 5059

35
[ 1220904-05-1 ]
[ 73852-17-2 ]
[ 1220904-06-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 110℃;Sealed tube;	Step 1; To a 20 mL vial was added bromide (100 mg, 0.19 mmol;prepared according to the procedures outlined in Scheme I), Pd(PPh3)4 (22 mg, 0.10 equiv.), the boronic acid (456 mg, 1.5 equiv.) and 0.5 mL of aq. NaHC03 solution, followed by 5 mL of toluene/EtOH (1/1 ). The vial was capped, sealed, and heated at 110 C overnight. The mixture was cooled to RT, diluted with ether, filtered through Celite, and concentrated. The residue was purified via gradient flash chromatography (ISCO, 0 - 50 % EtOAc in hexanes, S1O2) to furnish the desired compound (103 mg, 91% yield).

Reference： [1]Patent: WO2011/119559,2011,A1 .Location in patent: Page/Page column 157

36
[ 2042-37-7 ]
[ 73852-17-2 ]
[ 1383378-84-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3550 - 3553

37
[ 73852-17-2 ]
C₂₀H₁₅Cl₂N [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3550 - 3553

38
[ 73852-17-2 ]
[ 1383378-67-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3550 - 3553

39
[ 919758-97-7 ]
[ 73852-17-2 ]
[ 1426802-41-6 ]

Yield	Reaction Conditions	Operation in experiment
8 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In water; acetonitrile; at 100℃; for 0.5h;Inert atmosphere; Microwave irradiation; Sealed tube;	A mixture of <strong>[73852-17-2](2,6-dichlorophenyl)boronic acid</strong> (32.9 mg), N-(4-bromophenyI)-2-[4- (ethylsulfonyl)phenyl]acetamide (intennediate lb, 60 mg), PdC]2(dppf)-CH2CI2 adduct (12.8 mg) and Cs2C03 ( 1.4 mg) in acetonitrile (1.5 mL) and water (0.5 mL) was sealed in a vessel, and heated in the microwave at 100C for 30 mins. The mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by MDAP to afford N-(2',6'- dichloro-4-biphenylyl)-2-[4-(ethylsulfonyl)phenyl]acetamide (8 mg) as a yellow solid. ?-NMR (400 MHz, DMSO-.4) 5 ppm 1.10 (t, J= 7.2 Hz, 3Eta), 3.28 (q, J= 7.2 Hz, 2Eta), 3.83 (s, 2H), 7.20 (d, J= 8.4 Hz, 2H), 7.41 (t, J= 8.40 Hz, 1H)} 7.57 (d, J= 8.0 Hz, 2H), 7.63 (d, /= 8.4 Hz, 2H), 7.80 (d, J= 8.4 Hz, 2H), 7.86 (d, J= 8.0 Hz, 2H), 10.43 (s, 1H); MSiES4) m/z 448 (MH^).

Reference： [1]Patent: WO2013/29338,2013,A1 .Location in patent: Page/Page column 81; 82

40
[ 1575-37-7 ]
[ 73852-17-2 ]
[ 1430719-86-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3531 - 3545

41
[ 1575-37-7 ]
[ 73852-17-2 ]
[ 1430720-24-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3531 - 3545

42
[ 1395347-62-2 ]
[ 73852-17-2 ]
[ 1447249-91-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 4778 - 4791

43
[ 1613435-38-3 ]
[ 73852-17-2 ]
[ 1613435-42-9 ]

Yield	Reaction Conditions	Operation in experiment
12%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 135℃; for 16h;	3-(2,6-Dichlorophenyl)-1-methoxy-5-nitroisoquinoline (11e). To 3-bromo-1- methoxy-5-nitroisoquinoline 9 (240 mg, 0.85 mmol) in a dry flask was added tris(di- benzylideneacetone)dipalladium (78 mg, 0.085 mmol), 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl (79 mg, 0.17 mmol), <strong>[73852-17-2]2,6-dichlorobenzeneboronic acid</strong> (243 mg, 1.3 mmol) and potassium phosphate (541 mg, 2.5 mmol). Dry dimethylformamide (8.0 mL) was added and the mixture was stirred at 135C for 16 h. The mixture was filtered through Celite and the solvent was evaporated. Chromatography (ethyl acetate / petroleum ether 1 : 99) gave 3-(2,6-dichlorophenyl)-1-methoxy-5-nitroisoquinoline 11e (35 mg, 12%) as a yellow solid: mp 122-124C; 1H NMR (CDCI3) delta 4.17 (3 H, s, Me), 7.30 (1 H, t, J = 8.7 Hz, Ph 4-H), 7.44 (2 H, d, J = 8.5 Hz, Ph 3,5-H2), 7.66 (1 H, t, J = 8.1 Hz, 7-H), 8.08 (1 H, s, 4-H), 8.52 (1 H, dd, J = 7.8, 1.3 Hz, 6-H), 8.67 (1 H, dt, J = 8.2, 1.1 Hz, 8-H); 3C NMR (CDCI3) (HSQC / HMBC) delta 54.61 (Me), 11 1.16 (4-C), 120.08 (4a-C), 125.36 (7-C), 128.24 (Ph 3,5-C2), 128.56 (6-C), 129.82 (Ph 4-C), 130.75 (8a-C), 131.32 (8-C), 134.86 (Ph 2,6-C2), 138.19 (Ph 1-C), 144.94 (5-C), 149.95 (3-C), 160.73 (1-C); MS m/z 348.9740 (M - H) (C^Hn^C CINzOs requires 348.9961).
12%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 135℃; for 16h;	To 37 (240 mg, 850 mmol)was added Pd2dba3 (78 mg, 85 mmol), SPhos (79 mg, 170 mmol),<strong>[73852-17-2]2,6-dichlorobenzeneboronic acid</strong> (243 mg, 1.3 mmol) and K3PO4 (541 mg, 2.5 mmol). Dry DMF (8.0 mL) was added and the mixture wasstirred at 135C for 16 h. Filtration (Celite ), evaporation and chromatography (EtOAc / petroleum ether 1: 99) gave30n (35 mg, 12%) as a yellow solid: mp 122-124C; 1H NMR(CDCl3) d 4.17 (3 H, s, Me), 7.30 (1 H, t, J= 8.7 Hz, Ph 4-H), 7.44 (2 H, d, J =8.5 Hz, Ph 3,5-H2), 7.66 (1 H, t, J = 8.1 Hz, 7-H), 8.08 (1 H, s, 4-H), 8.52 (1 H, dd, J = 7.8, 1.3 Hz, 6-H), 8.67 (1 H, dt, J = 8.2, 1.1 Hz, 8-H); 13C NMR (CDCl3) (HSQC / HMBC) d 54.61(Me), 111.16 (4-C), 120.08 (4a-C), 125.36 (7-C), 128.24 (Ph 3,5-C2),128.56 (6-C), 129.82 (Ph 4-C), 130.75 (8a-C), 131.32 (8-C), 134.86 (Ph 2,6-C2),138.19 (Ph 1-C), 144.94 (5-C), 149.95 (3-C), 160.73 (1-C); MS m/z 348.9740 (M - H)- (C16H1135Cl37ClN2O3requires 348.9961).

Reference： [1]Patent: WO2014/87165,2014,A1 .Location in patent: Page/Page column 61
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5891 - 5908

44
[ 73852-17-2 ]
[ 1613435-20-3 ]

Reference： [1]Patent: WO2014/87165,2014,A1

45
[ 73852-17-2 ]
[ 1613435-21-4 ]

Reference： [1]Patent: WO2014/87165,2014,A1

46
[ 73852-17-2 ]
[ 541-73-1 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5365 - 5368

47
[ 4408-64-4 ]
[ 73852-17-2 ]
C₁₁H₁₀BCl₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	In N,N-dimethyl-formamide; at 130℃; under 15514.9 Torr; for 0.166667h;Microwave irradiation;	General procedure: The boronic acid (1 mmol) was added to a 10mL microwave vial equipped with a magnetic stirrer, followed by methyliminodiacetic acid (MIDA) (1 mmol) and dry DMF (1 mL) was added to the vial. The Teflon cap was added and the reaction mixture was heated using the dynamic heating method, with max power set to 300 W, max pressure 300 psi, max temperature 130 C, high stirring throughout and power max turned off. This method was used to hold the reaction mixture at 130 C for 10 min. After cooling, the DMF was removed under reduced pressure giving crude yellow oil. The latter was triturated via sonication with deionised water (5 mL), cooled in an ice bath and collected by filtration and washed with cold water (5 mL). This solid was then further triturated with diethyl ether (5 mL), cooled in an ice bath, collected by filtration and washed with diethyl ether (5 mL) then air dried giving pure product as a white precipitate.

Reference： [1]Tetrahedron,2014,vol. 70,p. 9125 - 9131

48
tert-butyl 4-(4-((6-iodo-8-methyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate [ No CAS ]
[ 73852-17-2 ]
tert-butyl 4-(4-((6-(2,6-dichlorophenyl)-8-methyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); at 80℃; for 18h;Sealed tube;	Pd2(dba)3 (3.9 mg, 3.91 imol) was added to a pre-degassed solution of 6- iodo-8-methyl-2-(methylthio)pyrido [2, 3-d]pyrimidin-5(8H) - one (44 mg, 0.078 mmol), <strong>[73852-17-2](2,6-dichlorophenyl)boronic acid</strong> (149 mg, 0.782 mmol), SPhos (2.6 mg, 6.26 mol) andpotassium phosphate, tribasic (50 mg, 0.235 mmol) in c,c,c-trifluorotoluene (2.0 mL) in a 10 mL vial. The vessel was sealed and the reaction mixture was stirred at 80 C for 18 h. The reaction mixture was cooled to RT and diluted with DCM and brine and extracted. The organicextracts were dried (Phase Separator) and concentrated before being purified by flash chromatography (0-100%, EtOAc in cyclohexane) to afford the title compound (30 mg, 66%) as an off-white solid. [N.B. the product contained 50% starting material but was used in thefinal step regardless] . LCMS (Method A) : = 1.47 mm, m/z = 581, 583 [M+H].

Reference： [1]Patent: WO2015/19037,2015,A1 .Location in patent: Page/Page column 71

49
6-iodo-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-5(8H)-one [ No CAS ]
[ 73852-17-2 ]
[ 1431323-90-8 ]

Yield	Reaction Conditions	Operation in experiment
10%		Pd2(dba)3 (4.2 mg, 4.6 imol) was added to a pre-degassed solution of 6-iodo-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 5(8H)-one (153 mg, 0.460 mmol), (2,6- dichlorophenyl)boronic acid (114 mg, 0.599 mmol), SPhos (7.6 mg, 0.018 mmol) and potassium phosphate, tribasic(293 mg, 1.38 mmol) in ,,-trifluorotoluene (2.0 mL) in a 10 mL vial. The vessel was sealed and the reaction mixture was stirred at 80 C. After 16 h, analysis by LCMS showed incomplete reaction. On increasing the temperature to 90 C, LCMS showed no further change.Further Pd(OAc)2 (4 mg) and SPhos (8 mg) were added. After a further 16 h, the solvents were removed in vacuo (Genevac EZ-2), the remaining residue was partitioned between EtOAc and sodium bicarbonate (aq) solution, separated, extracted (EtOAc x 2), and dried (PhaseSeparator) . The solvents were removed in vacuo and the remaining residue was purified by flash chromatography (0-100%, EtOAc in cyclohexane) to give the title compound(15.5 mg, 10%) as a white solid. LCMS (Method A) : =1.21 mi m/z = 352 [M+H].

Reference： [1]Patent: WO2015/19037,2015,A1 .Location in patent: Page/Page column 54; 55

50
[ 98495-32-0 ]
[ 73852-17-2 ]
3-(2,6-dichlorophenyl)-5-(3-pyridyl)-2,4-dihydro-1,2,4,3-triazaborole [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 74 - 77

51
[ 541-73-1 ]
[ 73852-17-2 ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5366 - 5372

52
[ 73852-17-2 ]
(2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5366 - 5372

53
[ 73852-17-2 ]
potassium (2,6-dichlorobenzene)trifluoroborate [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5366 - 5372

54
[ 73852-17-2 ]
C₁₈H₇BCl₂F₆ [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5366 - 5372

55
C₁₇H₁₈ClN₃O₄ [ No CAS ]
[ 73852-17-2 ]
C₂₃H₂₁Cl₂N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 120℃; for 2h;Microwave irradiation; Inert atmosphere;	Synthesis of compound 5.1. To a solution of compound 3.1 (0.2 g, 0.55mmol, 1.0 equiv) in 1,4-dioxane (8 mL) was added 2,6-dichloro phenylboronic acid (0.2 lg, l .lmmol, 2.0 equiv), water (2 mL) and diisopropylethylamine (0.4mL, 2.0mmol, 4.0 equiv). The mixture was degassed under argon gas for 10-15min then Pd(PPh3)4 (0.063g, 0.055mmol, 0.1 equiv) was added and the suspension was degassed under argon for 5 minutes. The mixture was heated to 120 C in a microwave for 2 hours. Upon completion, the mixture was poured into water and extracted with ethyl acetate. The organic layers were combined and dried over sodium sulfate. The solvent was removed under reduced pressure to obtain crude material, which was purified using preparative HPLC to furnish compound 5.1 (0.170 g, 65%). MS (ES): m/z 474 [M+H]+.

Reference： [1]Patent: WO2015/131080,2015,A1 .Location in patent: Paragraph 00300; 00301

56
C₁₉H₂₂ClN₃O₄ [ No CAS ]
[ 73852-17-2 ]
C₂₅H₂₅Cl₂N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 120℃; for 2h;Microwave irradiation; Inert atmosphere;	Synthesis of compound 6.2. To a solution of 6.1 (0.2 g, 0.51mmol, 1.0 equiv) in 1,4-dioxane (8 mL) was added <strong>[73852-17-2]2,6-dichloro-phenylboronic acid</strong> (0.194g, l .Ommol, 2.0 equiv), water (2 mL) and diisopropylethylamine (0.35mL, 2.0mmol, equiv). The mixture was degassed under argon gas for 15 minutes then Pd(PPh3)4 (0.059g, 0.051mmol, 0.1 equiv) was added and the suspension was heated at 120 C in a microwave oven for 2 hours. After consumption of the starting material, the mixture was poured into water and the product was extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to obtain the crude material. The crude batches were purified by preparative HPLC to furnish compound 6.2 (0.140 g, 8%). MS (ES): m/z 502 [M+H]+.

Reference： [1]Patent: WO2015/131080,2015,A1 .Location in patent: Paragraph 00305; 00307

57
[ 40248-84-8 ]
[ 73852-17-2 ]
2-((2,6-dichlorophenyl)thio)cyclohexa-2,5-diene-1,4-dione [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 5543 - 5546

58
[ 73852-17-2 ]
[ 87-65-0 ]

Reference： [1]Chemistry Letters,2016,vol. 45,p. 268 - 270

59
[ 946147-15-5 ]
[ 73852-17-2 ]
[ 946147-19-9 ]

Yield	Reaction Conditions	Operation in experiment
2.4 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In toluene; for 48h;Inert atmosphere; Reflux;	Step 1 To a 500 mL round flask was added 3-bromo-6,7-dimethylimidazo[1,2-f]phenanthridine (8.2 g, 25.2 mmol), <strong>[73852-17-2]2,6-dichlorophenylboronic acid</strong> (19.2 g, 100.9 mmol), Pd2(dba)3 (2.29 g, 2.5 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (S-Phos, 4.11 g, 10.0 mmol), potassium phosphate tribasic (26.7 g, 126 mmol), and 250 mL of toluene. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 48 hours. After cooling, the mixture was purified by a silica gel column. Yield of 3-(2,6-dichlorophenyl)-6,7-dimethylimidazo[1,2-f]phenanthridine was 2.4 g.
2.4 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; In toluene; for 48h;Reflux; Inert atmosphere;	Step 1 500 round flask for 3-bromo-6,7-dimethyl crude imidazole[1,2-f]phenanthridine (8.2 g, 25.2 mmol), <strong>[73852-17-2]2,6-dichlorophenylboronic acid</strong> (19.2 g, 100.9 mmol ), Pd2(dba)3 (2.29 g, 2.5 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(SPhos, 4.11 g, 10.0 mmol), potassium phosphate basic (26.7 g It was added to a toluene 126 mmol) and 250 . The reaction was heated to reflux, stirred for 48 hours under a nitrogen atmosphere. After cooling, the mixture was purified by a silica gel column. 3 is a (2,6-dichlorophenyl) -6,7-dimethylimidazolium crude [1,2-J] output of the phenanthridine was 2.4 g.

Reference： [1]Patent: US9281483,2016,B2 .Location in patent: Page/Page column 92
[2]Patent: KR2016/30582,2016,A .Location in patent: Paragraph 0245; 0246; 0247; 0248; 0249

60
[ 19230-28-5 ]
[ 109-63-7 ]
[ 73852-17-2 ]
bis(2,6-dichlorophenyl)iodonium tetrafluoroborate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4234 - 4237

61
[ 258-14-0 ]
[ 108-88-3 ]
[ 73852-17-2 ]
2C₆H₅BCl₂O₂*C₁₄H₈N₄*2C₇H₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 2710 - 2727

62
[ 254-60-4 ]
[ 73852-17-2 ]
C₆H₅BCl₂O₂*C₈H₆N₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 2710 - 2727

63
[ 66-71-7 ]
[ 73852-17-2 ]
C₆H₅BCl₂O₂*C₁₂H₈N₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 2710 - 2727

64
potassium hydrogen difluoride [ No CAS ]
[ 73852-17-2 ]
potassium (2,6-dichlorobenzene)trifluoroborate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 9512 - 9516
Angew. Chem.,2017,vol. 129,p. 9640 - 9644,5

65
[ 552331-06-3 ]
[ 73852-17-2 ]
3-chloro-6-(2,6-dichlorophenyl)isoquinoline [ No CAS ]