[ CAS No. 90002-36-1 ] {[proInfo.proName]}

Name: 90002-36-1|2-Ethylphenylboronic acid|97%
Brand: Ambeed
SKU: A148237
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2D 3D

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Quality Control of [ 90002-36-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 90002-36-1 ]

SDS Specification

Alternatived Products of [ 90002-36-1 ]

Product Details of [ 90002-36-1 ]

CAS No. :	90002-36-1	MDL No. :	MFCD02093075
Formula :	C₈H₁₁BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QSSPYZOSTJDTTL-UHFFFAOYSA-N
M.W :	149.98	Pubchem ID :	4100862
Synonyms :

Calculated chemistry of [ 90002-36-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.04
TPSA :	40.46 Å²

Pharmacokinetics

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) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.62
Log Po/w (WLOGP) :	-0.07
Log Po/w (MLOGP) :	0.94
Log Po/w (SILICOS-IT) :	0.02
Consensus Log Po/w :	0.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.06
Solubility :	1.3 mg/ml ; 0.00867 mol/l
Class :	Soluble
Log S (Ali) :	-2.08
Solubility :	1.24 mg/ml ; 0.00828 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.06
Solubility :	1.3 mg/ml ; 0.00869 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.45

Safety of [ 90002-36-1 ]

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 [ 90002-36-1 ]

* 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 [ 90002-36-1 ]
Downstream synthetic route of [ 90002-36-1 ]

[ 90002-36-1 ] Synthesis Path-Upstream 1~3

1
[ 103-63-9 ]
[ 90002-36-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2707 - 2718
[2] Patent: US2002/19527, 2002, A1,

2
[ 1973-22-4 ]
[ 90002-36-1 ]

Reference： [1] Chemistry - A European Journal, 2008, vol. 14, # 36, p. 11429 - 11441
[2] Organic Letters, 2005, vol. 7, # 7, p. 1291 - 1294

3
[ 109-72-8 ]
[ 150-46-9 ]
[ 1973-22-4 ]
[ 90002-36-1 ]

Reference： [1] Patent: US2003/195157, 2003, A1,
[2] Patent: US2004/127423, 2004, A1,

[ 90002-36-1 ] Synthesis Path-Downstream 1~88

1
[ 90002-36-1 ]
[ 724707-85-1 ]
[ 862885-66-3 ]

Reference： [1]Synlett,2005,p. 1601 - 1605
[2]Journal of Organic Chemistry,2006,vol. 71,p. 4956 - 4964

2
[ 914458-53-0 ]
[ 90002-36-1 ]
JWH-365 [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5432 - 5435

3
[ 622860-38-2 ]
[ 90002-36-1 ]
4-(2-Ethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4896 - 4911

4
[ 90002-36-1 ]
[ 14628-57-0 ]
4-(2-ethylphenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Reflux; Inert atmosphere;	To a mixture of 2.516 g of 4-chloro-5-methoxy-2- methyl-3 (2H) -pyridazinone, 2.575 g of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> and 3.333 g of sodium carbonate were added 30 mL of 1,4-dioxane and 20 mL of water. Further, 2.417 g of tetrabutylammonium bromide. and 0.657 g of tetrakis (triphenylphosphine) palladium were added thereto, and the mixture was then stirred with heating under reflux for 17 hours under a nitrogen atmosphere. The reaction mixture was cooled, 50 mL of water was added thereto, and extracted with 100 mL, followed by 30 mL of ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The resultant residue was washed with an ethyl acetate-hexane mixture solvent (1:2) to obtain 3.238 g of the titled compound as yellow crystals.
	With tetrabutylammomium bromide; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Reflux; Inert atmosphere;	To a mixture of 2.516 g of 4-chloro-5-methoxy-2- methyl-3 (2H) -pyridazinone, 2.575 g of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> and 3.333 g of sodium carbonate were added 30 mL of 1,4-dioxane and 20 mL of water. Further, 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis (triphenylphosphine) palladium were added thereto, and the mixture was then stirred with heating under reflux for 17 hours under a nitrogen atmosphere. The reaction mixture was cooled, 50 mL of water was added thereto, and extracted with 100 mL, followed by 30 mL of ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The resultant residue was washed with an ethyl acetate-hexane mixture solvent (1:2) to obtain 3.238 g of the titled compound as yellow crystals.
	With tetrabutylammomium bromide; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Reflux; Inert atmosphere;	To a mixture of 2.516 g of 4-chloro-5-methoxy-2- methyl-3 (2H) -pyridazinone, 2.575 g of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> and 3.333 g of sodium carbonate were added 30 mL of 1,4-dioxane and 20 mL of water. Further, 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis (triphenylphosphine) palladium were added thereto, and the mixture was then stirred with heating under reflux for 17 hours under a nitrogen atmosphere. The reaction mixture was cooled, 50 mL of water was added thereto, and extracted with 100 mL, followed by 30 mL of ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The resultant residue was washed with an ethyl acetate-hexane mixture solvent (1:2) to obtain 3.238 g of the titled compound as yellow crystals.

	With tetrabutylammomium bromide; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Reflux; Heating;	Reference Example 1 To a mixture of 2.516 g of 4-chloro-5-methoxy-2- methyl-3 (2H) -pyridazinone, 2.575 g of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> and 3.333 g of sodium carbonate, 30 mL of 1,4-dioxane and 20 mL of water were added. To this mixture, 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis (triphenylphosphine) palladium were added, followed by heating under reflux under a nitrogen atmosphere for 17 hours. After the reaction mixture was cooled, 50 mL of water was added, followed by extraction sequentially with 100 mL of ethyl acetate and 30 mL of ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated. The residue was washed with an ethyl acetate-hexane mixed solvent (1:2) to obtain 3.238 g of 4- (2-ethylphenyl) -5-methoxy-2-methyl-3 (2H) -pyridazinone [compound II-l] as a yellow crystal.
	With tetrabutylammomium bromide; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Reflux; Inert atmosphere;	Reference Example 1 To a mixture of 2.516 g of 4-chloro-5-methoxy-2-methyl-3(2H)-pyridazinone, 2.575 g of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> and 3.333 g of sodium carbonate were added 30 mL of 1,4-dioxane, 20 mL of water, 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis(triphenylphosphine)palladium. This mixture was heated under reflux for 17 hours under nitrogen atmosphere. The reaction mixture was cooled. 50 mL of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried with anhydrous magnesium sulfate, and concentrated. The resulting solid was washed with a mixed solvent of ethyl acetate-hexane (1:2), to give 3.238 g of 4-(2-ethylphenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone [compound (II-1)] as a yellow crystal.
	With tetrabutylammomium bromide; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Heating / reflux;	Reference example 1 4- (2-Ethylphenyl) -5-methoxy-2-methyl-3 (2H) -pyridazino ne (Compound II-l); To a mixture of 2.516 g of 4-chloro-5-methoxy-2-methyl-3 (2H) -pyridazinone, 2.575 g of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> and 3.333 'g of sodium carbonate were added 30 mL of 1,4-dioxane and 20 mL of water. To the mixture were added 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis (triphenylphosphine) palladium, and then under a nitrogen atmosphere, the resulting mixture was stirred and heated under reflux for 17 hours.. After cooling, 50 mL of water was added to the reaction mixture, which was extracted with 100 mL of ethyl acetate and then 30 mL of ethyl acetate. The extracts were combined, washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The solid obtained was washed with a mixed solvent of ethyl acetate and hexane (1:2) to yield '3.238 g of the title compound as yellow crystals.

Reference： [1]Patent: WO2009/35145,2009,A2 .Location in patent: Page/Page column 80
[2]Patent: WO2009/35146,2009,A2 .Location in patent: Page/Page column 80
[3]Patent: WO2009/35151,2009,A2 .Location in patent: Page/Page column 78
[4]Patent: WO2010/104216,2010,A1 .Location in patent: Page/Page column 99-100
[5]Patent: US2012/28988,2012,A1 .Location in patent: Page/Page column 35
[6]Patent: WO2007/119434,2007,A1 .Location in patent: Page/Page column 68

5
[ 95-56-7 ]
[ 90002-36-1 ]
[ 952685-39-1 ]

Yield	Reaction Conditions	Operation in experiment
31%	With 4 A molecular sieve; copper diacetate; In dichloromethane; at 20℃; for 48h;	Step 1. l-Bromo-2-(2-ethylphenoxy)benzene. To a solution of <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (4.50 g, 30 mmol), 2- bromophenol (3.54 g, 20 mmol), and Cu(OAc)2 (1.86 g, 10 mmol) in anhydrous CH2Cl2 (50 mL) were added activated 4 A molecular sieves (~ 0.5 g), followed by anhydrous Et3N (7.0 mL, 50 mmol). The resulting dark green solution was stirred at rt for 48 h. The solvent was removed under vacuum and the residue was triturated <n="90"/>several times with ether (~ 200 mL). The combined organic solutions were washed with satd aq NH4Cl, and 1 N aq HCl aqueous solution, and solvent was removed under vacuum to give a crude product. Flash column chromatography gave 1- bromo-2-(2-ethylphenoxy)benzene (1.72 g, 31 %) as a clear oil; 1H NMR (CDCl3, 400MHz) delta: 7.62 (dd, 1 H), 7.28 (m, 1 H), 7.22-7.08 (m, 3 H)5 6.96 (m, 1 H), 6.78 (m, 2 H), 2.64 (q, 2 H), 1.22 (t, 3 H); MS no ionization was observed.

Reference： [1]Patent: WO2007/117557,2007,A2 .Location in patent: Page/Page column 88-89

6
[ 90002-36-1 ]
2-(2,4-dichloro-phenylamino)-2-(2-ethyl-phenyl)-<i>N</i>-(2-pyridin-4-yl-ethyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2426 - 2429

7
[ 16732-64-2 ]
[ 90002-36-1 ]
[ 861213-76-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 16h;Heating / reflux;	a) 4- (2-Ethylphenyl)-indole-2-carboxylic acid; To a mixture of 0.28 g of <strong>[16732-64-2]4-bromo-indole-2-carboxylic acid</strong> and 0.069 g of tetrakistriphenylphosphinepalladium in 11 ml of toluene and 2 ml of 2M soda is added a solution of 0.300 g of 2-ethylphenylboronic acid in 3 ml of ethanol. This mixture is refluxed for 16 h, filtered and the aqueous phase acidified with 2N HCI and extracted with ethyl acetate. Concentration of the organic phase gives the product as a brownish powder, m. p. 230-233, sufficiently pure for the next step.

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107
[2]Patent: WO2005/70886,2005,A1 .Location in patent: Page/Page column 5

8
[ 904297-82-1 ]
[ 90002-36-1 ]
[ 904297-84-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation;	A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid-t-butyl ester (2.00 g, 6.55 mmol) in DME (16 ml)/2M Na2CO3 (11.46 ml, 22.93 mmol) was treated with <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (1.96 g, 13.10 mmol), and Pd[PPh3]4 (757 mg, 0.655 mmol) in a microwave oven at 150 C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 5-20% ethyl acetate/hexanes gradient to afford 1.25 g of colorless oil (t-butyl ester). This material was dissolved in 4N HCl/dioxane (10 ml) and stirred at rt overnight. Concentration under reduced pressure afforded the product as colorless oil (1.08 g, 60%).

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 12

9
[ 904297-87-6 ]
[ 90002-36-1 ]
benzoic acid N'-[2-(2'-ethyl-5-fluoro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 12h;	A solution of benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide (50 mg, 0.122 mmol) in DME (3 ml)/2M Na2CO3 (0.215 ml, 0.427 mmol) was treated with <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (27 mg, 0.183 mmol) and Pd[PPh3]4 (27 mg, 0.024 mmol) for 12 hours at 90 C. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-30% ethyl acetate/hexanes gradient to afford the product (19 mg, 36%). MS m/e 435.44 (M+H+)

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 21; 22

10
[ 904297-94-5 ]
[ 90002-36-1 ]
benzoic acid N'-[2-(2'-ethyl-5-methyl-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation;	A solution of benzoic acid N'-[2-(2-bromo-4-methyl-phenoxy)-acetyl]-N'-isopropyl-hydrazide (100 mg, 0.247 mmol) in DME (3 ml)/2M Na2CO3 (0.435 ml, 0.8645 mmol) was treated with <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (74 mg, 0.493 mmol), Pd[PPh3]4 (29 mg, 0.0247 mmol in a microwave oven at 150 C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-40% ethyl acetate/hexanes gradient to afford the product as a white solid (77 mg, 72%). MS m/e 431.34 (M+H+)

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 24

11
[ 904297-96-7 ]
[ 90002-36-1 ]
benzoic acid N'-[2-(2'-ethyl-4,5-difluoro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation;	A solution of benzoic acid N'-[2-(2-bromo-4,5-difluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide (100 mg, 0.234 mmol) in DME (3 ml)/2M Na2CO3 (0.435 ml, 0.864 mmol) was treated with <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (70 mg, 0.468 mmol) and Pd[PPh3]4 (27 mg, 0.0234 mmol) in a microwave oven at 150 C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-40% ethyl acetate in hexanes gradient to afford the product as a white solid (77 mg, 73%). MS m/e 453.30 (M+H+)

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 24

12
[ 904297-97-8 ]
[ 90002-36-1 ]
benzoic acid N'-[2-(2'-ethyl-3,5-difluoro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation;	A solution of benzoic acid N'-[2-(2-bromo-4,6-difluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide (100 mg, 0.234 mmol) in DME (3 ml)/2M Na2CO3 (0.410 ml, 0.819 mmol) was treated with <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (71 mg, 0.468 mmol), and Pd[PPh3]4 (27 mg, 0.0234 mmol) in a microwave oven at 150 C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-40% ethyl acetate/hexanes gradient to afford the product as a white solid (70 mg, 66%). MS m/e 453.30 (M+H+)

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 24; 25

13
[ 904297-98-9 ]
[ 90002-36-1 ]
benzoic acid N'-[2-(5-cyano-2'-ethyl-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation;	A solution of benzoic acid N'-[2-(2-bromo-4-cyano-phenoxy)-acetyl]-N'-isopropyl-hydrazide (200 mg, 0.480 mmol) in DME (3 ml)/2M Na2CO3 (0.840 ml, 1.68 mmol) was treated with <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (144 mg, 0.9608 mmol) and Pd[PPh3]4 (55 mg, 0.048 mmol) in a microwave oven at 150 C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with 30% ethyl acetate/hexanes to afford the product as a white solid (177 mg, 84%). MS m/e 442.25 (M+H+)

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 25

14
[ 109-72-8 ]
[ 150-46-9 ]
[ 1973-22-4 ]
[ 90002-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; ethyl acetate;	EXAMPLE 9 General Synthesis of Various Fmoc-biphenylalanine Derivatives Synthesis of various biphenyl alanine derivatives were carried out using the above described procedure, starting with the commercially available phenol derivative (e.g. Boc-Tyrosine methyl ester) to prepare the triflate and using the appropriate boronic acid to prepare the biphenylalanine analogs. When a required boronic acid was not available from commercial sources the synthesis of this intermediate was carried out as exemplified in the following example. 2-Ethylphenyl boronic acid: To a solution of 25 g (135 mmol) of 1-bromo-2-ethylbenzene in 280 mL of dry tetrahydrofuran, kept at -78 C. in an oven-dried 3 neck flask, was added slowly (keeping the temperature below -68 C.) 67.5 mL of 2.5N n-Butyl lithium in hexanes solution (169 mmol, 1.25 eq.). The reaction was stirred for an additional 1 h, and then 69 mL (405 mmol, 3 eq.) of triethylborate was added slowly, keeping the temperature below -68 C. The reaction was stirred for an additional 40 minutes and then the dry ice bath was removed, the reaction was allowed to warm up to room temperature, and then was poured into 300 mL of ice cold saturated ammonium chloride solution. 200 mL of ice cold ethyl acetate was added, and the mixture stirred for another 30 min. The layers were separated. The organic layer was washed with water, and brine. It was then dried over magnesium sulfate, and concentrated to give 19 g (92% yield) of product. The boronic acid was used without purification in the next step.
	In tetrahydrofuran; ethyl acetate;	EXAMPLE 9 General Synthesis of Various Fmoc-biphenylalanine Derivatives Synthesis of various biphenyl alanine derivatives were carried out using the above described procedure, starting with the commercially available phenol derivative (e.g. Boc-Tyrosine methyl ester) to prepare the triflate and using the appropriate boronic acid to prepare the biphenylalanine analogs. When a required boronic acid was not available from commercial sources the synthesis of this intermediate was carried out as exemplified in the following example. 2-Ethylphenyl boronic acid: To a solution of 25 g (135 mmol) of 1-bromo-2-ethylbenzene in 280 mL of dry tetrahydrofuran, kept at -78 C. in an oven-dried 3 neck flask, was added slowly (keeping the temperature below -68 C.) 67.5 mL of 2.5N n-Butyl lithium in hexanes solution (169 mmol, 1.25 eq.). The reaction was stirred for an additional 1h, and then 69 mL (405 mmol, 3 eq.) of triethylborate was added slowly, keeping the temperature below -68 C. The reaction was stirred for an additional 40 minutes and then the dry ice bath was removed, the reaction was allowed to warm up to room temperature, and then was poured into 300 mL of ice cold saturated ammonium chloride solution. 200 mL of ice cold ethyl acetate was added, and the mixture stirred for another 30 min. The layers were separated. The organic layer was washed with water, and brine. It was then dried over magnesium sulfate, and concentrated to give 19 g (92% yield) of product. The boronic acid was used without purification in the next step.

Reference： [1]Patent: US2003/195157,2003,A1
[2]Patent: US2004/127423,2004,A1

15
N-(4-(4-acetylpiperazin-1-yl)butyl)-4-bromobenzamide [ No CAS ]
[ 90002-36-1 ]
C₂₅H₃₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.166667h;Microwave;	N-(4-(4-acetylpiperazin-l-yl)butyl)-4-bromobenzamide (86 mg, 0.225 mmol) was dissolved in DME:EtOH 1 : 1 (20 mL) and added to a microwave tube containing <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (34 mg, 0.225 mmol). IM Na2CO3 in H2O was added (300 mul, 0.3 mmol) followed by Pd(PPh3)4 (26 mg, 0.0225 mmol). The tube was capped, shaken by hand and loaded into the microwave for 10 mins at 150 0C. The reaction was filtered through celite and washed with MeOH. The filtrate was concentrated in-vacuo and purified by reverse phase preparative HPLC. The product was taken on directly to form the HCl salt: 200 mul 1.25 M HCl in MeOH and 800 mul dichloromethane were added to the title compound and the solution was shaken and concentrated in- vacuo to afford the hydrochloride salt (38.7 mg). MS (ES) m/z 408

Reference： [1]Patent: WO2006/8133,2006,A2 .Location in patent: Page/Page column 30

16
[ 913297-44-6 ]
[ 90002-36-1 ]
[ 913298-33-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In toluene; at 100℃; for 4h;	mixture of 280 mg (1.23 mmol) of 7-bromo-l-methyl- l,3-dihydro-2No.-benzimidazol-2-one, 222 mg (1.48 mmol) of 2- ethylphenylboronic acid, 113 mg (0.0123 mmol) of tris (dibenzylideneacetone) dipalladium, 29 mg (0.0615 mmol) of X-Phos and 522 mg (2.46 mmol) of potassium phosphate in 9 mL of toluene was stirred at 100 0C for 4 hours. After cooling, the reaction mixture was diluted with water and ethyl acetate and passed through celite. The filtrate was extracted with ethyl acetate (X2) . The combined organic layer was washed with brine (Xl) , dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-65% ethylacetate/n-hexane gradient mixture to give 200 mg (64%) of the title compound. 1H NMR (CDCl3) delta 1.04 (3H, t, J = 7.7 Hz), 2.34-2.52 (2H, m) , 2.84 (3H, s) , 6.86-6.98 (2H, m) , 7.05-7.08 (2H, m) , EPO <DP n="120"/>7.18-7.39 (3H, m), 8.58 (IH, br s). MS Calcd. : 252; Found: 253 (M+H) .

Reference： [1]Patent: WO2006/116412,2006,A2 .Location in patent: Page/Page column 118; 119

17
[ 917873-75-7 ]
[ 90002-36-1 ]
1-[5-ethyl-4-(2-ethyl-phenyl)-thiophen-2-yl]-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80℃; for 8h;	d) 1 -(4-Bromo-5-ethyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1 - one (45 mg, 123 mumol) and <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (22 mg, 148 mumol) are dissolved in degassed dioxane (0.8 mL) and degassed 2 M aq. Na2CO3 solution. To this solution PdCI2(dppf) (5 mg, 7 mumol) is added under a stream of argon. The mixture is stirred at 80C for 8 h. The mixture is cooled to rt and an aliquot is purified by prep. HPLC to give 1 -[5-ethyl-4-(2-ethyl-phenyl)-thiophen-2-yl]-3-(4-hydroxy-3,5- dimethyl-phenyl)-propan-1 -one as a colourless resin; LC-MS: XR = 1.10 min, [M+1 ]+ = 383.25.

Reference： [1]Patent: WO2006/137019,2006,A1 .Location in patent: Page/Page column 42

18
[ 523-27-3 ]
[ 90002-36-1 ]
[ 956350-63-3 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7689 - 7692

19
[ 90002-36-1 ]
[ 180404-96-0 ]
[ 1012309-81-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 2198 - 2205

20
[ 90002-36-1 ]
[ 13453-32-2 ]
[ 35473-62-2 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 521 - 525

21
[ 90002-36-1 ]
[ 13453-32-2 ]
[ 89787-06-4 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 521 - 525

22
[ 1028330-89-3 ]
[ 90002-36-1 ]
[ 1028330-95-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile;Microwave irradiation;	To (2-chloro-4-methoxy-5,6,7,8-tetrahydro-quinolin-5-yl)-ethyl-naphthlen-1-yl-amine (20.9 mg, 57.0 mumol, 1 equiv) was added <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (12.8 mg, 85.5 mumol, 1.5 equiv), PdCl2(PPh3)2 (2.0 mg, 2.8 mumol, 0.05 equiv), an aqueous solution of Na2CO3 (2 M, 200 muL), and CH3CN (200 muL). The resulting mixture was heated by microwave irradiation (130 C., 15 minutes, 250 W). The mixture was then partially concentrated, to remove organic solvent. The residual mixture was diluted with water (2 mL) and extracted with CH2Cl2 (3×2 mL). The organic extracts were dried, filtered, and concentrated, The title compound (12.9 mg, 52%) was isolated from the residue by flash column chromatography (SiO2, 0-20% EtOAc in hexanes).

Reference： [1]Patent: US2009/48295,2009,A1 .Location in patent: Page/Page column 28
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2544 - 2548

23
(8aR)-octahydropyrrolo[1,2-a]pyrazine dihydrochloride [ No CAS ]
[ 90002-36-1 ]
[ 298-12-4 ]
(R)-(2-ethylphenyl)[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]acetic acid hydrochloride [ No CAS ]
(S)-(2-ethylphenyl)[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]acetic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 151 : (2-ethylphenyl)[(8af?)-hexahvdropyrrolo[1 ,2-a]pyrazin-2(1 H)-yl1acetic acid hydrochloride; A mixture of 188 mg of <strong>[90002-36-1](2-ethylphenyl)boronic acid</strong> (1.25 mmole, Aldrich), 250 mg of (8aR)-octahydropyrrolo[1 ,2-a]pyrazine di-hydrochloride (intermediate 1 15, 1.25 mmole),116 mg of glyoxylic acid monohydrate (1.25 mmole, Aldrich) and 347 mg of K2CO3 (2.51 mmole) in 6 mL of CH3CN was heated under microwave irradiation at 12O0C for 20 min.Then, the solvent was removed and the residue was treated with HCI 1 N, charged on aHLB column and eluted with a gradient from 100% H2O to 100% MeOH. Solvents were removed under reduced pressure to give the title compound as a mixture of two diastereoisomers (260 mg, 57%). UPLC-MS [Acquity UPLC BEH C18, 50x21 mm, 1.7 mum, gradient: A: H2O +0.1 % HCOOH/B: MeCN+0.075% HCOOH: 1 % to 6%B in 0.2 min.,6% to 60%B in 1.05 min, 60% to 100%B in 0.5 min., 100%B for 0.2 min, flow rate: 1 ml/min]: R1 = 0.44 min. (91%) m/z (ES): 289.1 [M+H]+.

Reference： [1]Patent: WO2008/148853,2008,A1 .Location in patent: Page/Page column 164

24
[ 1152473-84-1 ]
[ 90002-36-1 ]
[ 1152473-80-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With water; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In propan-1-ol; toluene; at 90℃; for 30h;	To a mixture of compound 26 (60 mg, assumed 0.126 mmol), 2- ethylbenzeneboronic acid (23 mg, 0.153 mmol) and Pd[PPh3]4 (7.3 mg, 0.0063 mmol) was added toluene (0.9 mL) and «-propanol (0.3 mL) followed by 2 M aqueous Na2CO3 (0.19 mL, 0.38 mmol). The mixture was then heated at 90 0C for 30 h. After cooling to room temperature, saturated aqueous NaHCO3 was added and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with water, brine then dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography with 40% ethyl acetate/petroleum ether as eluent to afford compound 22 as a yellow foam (38 mg, 86%).

Reference： [1]Patent: WO2009/62258,2009,A1 .Location in patent: Page/Page column 94

25
[ 576-22-7 ]
[ 90002-36-1 ]
[ 1154423-84-3 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 4013 - 4016

26
[ 21524-34-5 ]
[ 90002-36-1 ]
[ 1154423-78-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 4013 - 4016

27
[ 523-27-3 ]
[ 90002-36-1 ]
[ 956350-63-3 ]
[ 1112196-99-2 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 11429 - 11441

28
[ 90002-36-1 ]
[ 6299-83-8 ]
C₁₄H₁₅N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6590 - 6605

29
[ 1073630-64-4 ]
[ 90002-36-1 ]
[ 1073629-74-9 ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; dimethyl sulfoxide; at 80℃; for 15h;	Add 0.50 ml of 2 M aqueous sodium carbonate solution to a mixture of 224 mg (0.50 mmol) 6-[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester and 18 mg (0.03 mmol) bis(triphenylphosphine)palladium(II) chloride in 11.2 ml DMSO. Next, add 187 mg (1.25 mmol) <strong>[90002-36-1](2-ethylphenyl)boronic acid</strong> and stir the mixture for 15 h at 80 C. Filter the reaction mixture and purify directly by preparative RP-HPLC (gradient: water/acetonitrile). 69 mg (29% of theor.) of the desired product is obtained.LC-MS (Method 2): Rt=2.83 min; m/z=474 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=8.33 (s, 1H), 7.39-7.31 (m, 2H), 7.26-7.17 (m, 4H), 6.98 (d, 2H), 5.42 (t, NH), 3.76 (s, 3H), 3.58 (s, 3H), 3.41 (q, 2H), 2.49 (q, 2H), 2.29 (t, 2H), 1.55-1.44 (m, 4H), 1.27-1.19 (m, 2H), 1.00 (t, 3H).

Reference： [1]Patent: US2009/318475,2009,A1 .Location in patent: Page/Page column 73

30
[ 875639-15-9 ]
[ 90002-36-1 ]
[ 329214-79-1 ]
3-(2-ethyl-phenyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		Step 1: Synthesis of 3-(2-ethyl-phenyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine To 5-bromo-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (15 mg, 0.0314 mmol, prepared as described in method 1), <strong>[90002-36-1]2-ethylphenyl boronic acid</strong> (5.2 mg, 0.034 mmol), and dichlorobis (triphenylphosphino)palladium (II) (1.3 mg, 0.0002 mmol) in a Smith process vial was added 0.5 mL of a 1:1 mixture of acetonitrile, and a 2 M solution of sodium carbonate in water. The reaction mixture was stirred for 6 h, then 3-pyridyl boronic acid pinacol ester (8.4 mg, 0.041 mmol) and dichlorobis (triphenylphosphino)palladium (II) (1.3 mg, 0.0002 mmol) were added and the reaction was run in a Personal Chemistry microwave reactor at 150 C. for 900 s. The mixture was diluted with DMF (2 mL), filtered on a silica plug, and solvent was evaporated. Purification by reverse phase chromatography using a gradient of H2O and acetonitrile (with 0.1% formic acid as a modifier) afforded 3-(2-ethyl-phenyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine as a solid (5.8 mg, 61% yield). 1H NMR (500 MHz, DMSO-d6) delta 1.05 (t, J=7.5 Hz, 3H), 2.66 (q, J=7.5 Hz, 2H), 7.27 (t, J=7.0 Hz, 1H), 7.31 (t, J=7.0 Hz, 1H), 7.38 (d, J=7.5 Hz, 2H), 7.45 (dd, J=5.5, 8.5 Hz, 1H), 7.60 (s, 1H), 7.98 (d, J=2.0 Hz, 1H), 8.10 (dd, J=1.5, 8.0 Hz, 1H), 8.54 (d, J=5.0 Hz, 1H), 8.60 (d, J=2.0 Hz, 1H), 8.90 (s, 1H), 12.0 (s, 1H). MS: m/z 300 (M+H+).

Reference： [1]Patent: US2006/30583,2006,A1 .Location in patent: Page/Page column 99

31
[ 1182349-28-5 ]
[ 90002-36-1 ]
[ 1182349-31-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107

32
[ 5194-37-6 ]
[ 90002-36-1 ]
[ 1182349-09-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107

33
[ 1013-83-8 ]
[ 90002-36-1 ]
[ 1182349-10-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107

34
[ 41252-95-3 ]
[ 90002-36-1 ]
[ 1182349-34-3 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107

35
[ 90002-36-1 ]
[ 167478-92-4 ]
[ 1182349-44-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107

36
C₄₈H₅₂IN₄O₈Pol [ No CAS ]
[ 90002-36-1 ]
C₅₆H₆₁N₄O₈Pol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7788 - 7799

37
[ 1141473-84-8 ]
[ 90002-36-1 ]
[ 1196973-59-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 12h;Inert atmosphere;	methyl 2'-ethyl-2-(methoxymethyl)-1 , 1 '-biphenyl-4-carboxylate To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate, (Intermediate 28, step 2) (12 g, 0.0463 mol) in toluene (150 ml_) and water (35 ml_) under N2, was added 2-ethyl benzene boronic acid (9.02 g, 0.0601 mol) followed by potassium carbonate (19 g, 0.1389 mol) and Pd(PPh3)4 (2.67g, 0.0023 mol). The reaction mixture was degassed with N2 for 10 min before heating. After 12 hours at 1000C, the reaction mixture was diluted with EtOAc. The organic layer was washed with sodium bicarbonate sat. solution (1x100 ml_), water (2x100 ml_) and finally with brine (1x100 ml_). It was then dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography (silica gel, 60-120 mesh, eluting with pet ether/ EtOAc) to afford the title compound as a pale yellow liquid (12 g, 83%). 1H NMR (CDCI3, 400 MHz) delta 8.24-8.26 (1 H, s), 7.99-8.01 (1 H, d), 7.32-7.38 (2H, m), 7.22- 7.27 (2H, m), 7.07-7.09 (1 H, d), 4.12-4.21 (2H, d), 3.93-3.95 (3H, s), 3.28-3.30 (3H, s), 2.28- 2.43 (2H, m), 1.01-1.05 (3H, t).
53%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃;Inert atmosphere of N2;	Intermediate A1 step 2) in toluene (150 ml.) and water (35 ml.) was added 2-ethyl benzene boronic acid (9.0 g, 60.1 mmol) followed by potassium carbonate (19.0 g, 139 mmol) and Pd(PPh3)4 (2.7 g, 2.3 mmol). The resulting mixture was degassed with N2 for 10 min and heated at 1000C for 12 hours. The reaction mixture was diluted with EtOAc. The organic layer was washed with a saturated aqueous solution of NaHCO3, water (2x) and brine, and then dried (Na2SO4). The solvents were removed under reduced pressure. The residue was purified by chromatography (silica, pet ether/ EtOAc) to afford the title compound as a pale yellow oil (12.0 g, 83%). 1H NMR (CDCI3, 400 MHz) delta 8.25 (1 H, s), 8.00 (1 H, d), 7.35 (2H, m), 7.25 (2H, m), 7.08 (1 H, d), 4.17 (2H, m), 3.94 (3H, s), 3.29 (3H, s), 2.43-2.28 (2H, m), 1.03 (3H, t).

Reference： [1]Patent: WO2010/69949,2010,A1 .Location in patent: Page/Page column 71
[2]Patent: WO2010/100142,2010,A1 .Location in patent: Page/Page column 53

38
[ 90002-36-1 ]
[ 73177-97-6 ]
[ 1222531-90-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3332 - 3338

39
[ 6781-98-2 ]
[ 90002-36-1 ]
[ 1154423-84-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; C22H26NOP; In 1,4-dioxane; at 110℃; for 24h;Inert atmosphere;Catalytic behavior;	A stock solution of Pd2(dba)3 (1.0 mol%, 0.0023 g) with L3 (4.0 mol%, 0.0099 g) in freshly distilled dioxane (5.0 ml) was initially prepared by continuously stirring at room temperature for 10 mm. 1 ml of the stock solution was transferred to another nitrogen-filled tube for further dilution. Freshly distilled dioxane was then added to the tube to give the needed concentration of palladium complex in total 4 ml final solution volume. 2-Chloro-1,3-dimethylbenzene (0.5 mmol, 0.07 g), <strong>[90002-36-1](2-ethylphenyl)boronic acid</strong> (1.0 mmol, 0.15 g, 2.0 equiv.), potassium phosphate tribasic monohydrate (1.5 mmol, 0.345 g, 3.0 equiv.) and magnetic stirrer bar were charged to another Schlenk tube. The tube was carefully evacuated and backfilled with nitrogen (3 cycles). 1 ml of the diluted stock solution was then transferred to Schlenk tube via syringe. The tube was then placed into a preheated oil bath (110 C) and stirred for 24 hours. The reaction was cooled down to room temperature and quenched with water and diluted with ethyl acetate. The organic phase was separated, washed, concentrated, and purified by column chromatography to provide pure desired product 2?-ethyl-2,6-dimethyl-1,1?-biphenyl as an off-white solid (0.1 g, 0.475 mmol, 95%).

Reference： [1]Chemical Communications,2011,vol. 47,p. 5079 - 5081
[2]Journal of Organic Chemistry,2013,vol. 78,p. 11513 - 11524
[3]Patent: WO2017/193288,2017,A1 .Location in patent: Page/Page column 15
[4]Chemistry - A European Journal,2010,vol. 16,p. 7996 - 8001

40
[ 591-50-4 ]
[ 90002-36-1 ]
[ 1812-51-7 ]

Reference： [1]Catalysis Letters,2010,vol. 137,p. 69 - 73

41
[ 609-73-4 ]
[ 90002-36-1 ]
[ 683238-57-5 ]

Reference： [1]Catalysis Letters,2010,vol. 137,p. 69 - 73

42
[ 1240662-86-5 ]
[ 90002-36-1 ]
1-(2-ethylphenyl)-N-(2-phenyl-2-propyl)-2-naphthamide [ No CAS ]
1-(2-ethylphenyl)-N-(2-phenyl-2-propyl)-2-naphthamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11278 - 11287

43
[ 1240662-88-7 ]
[ 90002-36-1 ]
2'-ethyl-6-methyl-N-(2-phenyl-2-propyl)-[1,1'-biphenyl]-2-carboxamide [ No CAS ]
2'-ethyl-6-methyl-N-(2-phenyl-2-propyl)-[1,1'-biphenyl]-2-carboxamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11278 - 11287

44
[ 1244469-19-9 ]
[ 90002-36-1 ]
[ 1244469-06-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5927 - 5933

45
[ 107317-58-8 ]
[ 90002-36-1 ]
[ 1246527-14-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With cesium fluoride;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In 1,4-dioxane; water; at 90℃; for 2.5h;	A mixture of <strong>[107317-58-8]methyl 4-bromo-3-(trifluoromethyl)benzoate</strong> (3.0 g, 10.6 mmol), 2- ethylphenylboronic acid (2.38 g, 15.9 mmol), cesium fluoride (4.83 g, 31.8 mmol), palladium acetate (48 mg, 0.21 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (261 mg, 0.64 mmol) was prepared in dioxane (30 mL) and water (15 mL), and then heated at 900C for 2.5 hours. The reaction mixture was diluted with MTBE (150 mL) and washed with water (50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (75 mL). The organic layers were combined, dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica, heptane/EtOAc), the title compound was obtained as a colorless oil (3.05 g, 93%). HPLC (Method A) Rt 5.6 min (Purity: 97.3%).

Reference： [1]Patent: WO2010/112461,2010,A1 .Location in patent: Page/Page column 84; 85

46
C₂₉H₂₉ClFIN₃O₄Pol [ No CAS ]
[ 90002-36-1 ]
C₃₇H₃₈ClFN₃O₄Pol [ No CAS ]

Reference： [1]Peptides,2010,vol. 31,p. 1353 - 1360

47
[ 1282516-62-4 ]
[ 90002-36-1 ]
[ 1282513-43-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 140℃; for 0.166667h;Microwave irradiation;	Example 297 methyl 2-(2-ethylphenyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate 297 Methyl 2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (80 mg, 1 eq), <strong>[90002-36-1]2-ethylphenylboronic acid</strong> (60 mg, 1.75 eq), and tetrakis(triphenylphosphine)palladium (10 mg, 0.05 eq), in 1.0 M aqueous sodium carbonate (1.0 mL) and acetonitrile (1.0 mL) were heated to 140 C. for 10 min in a sealed microwave reactor. The crude reaction mixture was concentrated and purified using reverse phase HPLC to yield 297 (11 mg). ESI-MS: 349.1 (M)+

Reference： [1]Patent: US2011/76292,2011,A1 .Location in patent: Page/Page column 226

48
[ 1207-69-8 ]
[ 90002-36-1 ]
[ 1308652-73-4 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 5079 - 5081

49
[ 716-53-0 ]
[ 90002-36-1 ]
[ 1112196-99-2 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 5079 - 5081

50
[ 1319741-16-6 ]
[ 90002-36-1 ]
[ 1310064-12-0 ]

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

51
[ 930-68-7 ]
[ 90002-36-1 ]
[ 1309435-09-3 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3182 - 3185

52
[ 916792-13-7 ]
[ 90002-36-1 ]
[ 1335222-90-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5171 - 5176

53
[ 916792-13-7 ]
[ 90002-36-1 ]
[ 1335223-17-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5171 - 5176

54
[ 90002-36-1 ]
[ 99685-96-8 ]
[ 1269525-54-3 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 590 - 598

55
[ 90002-36-1 ]
[ 105-36-2 ]
[ 105337-78-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8107 - 8112

56
[ 90002-36-1 ]
5-benzoyloxy-4-(2-ethylphenyl)-2-methyl-3(2H)-pyridazinone [ No CAS ]

Reference： [1]Patent: WO2007/119434,2007,A1
[2]Patent: US2012/28988,2012,A1

57
[ 90002-36-1 ]
4-(2-ethylphenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone [ No CAS ]

Reference： [1]Patent: WO2007/119434,2007,A1
[2]Patent: US2012/28988,2012,A1

58
[ 1366180-89-3 ]
[ 90002-36-1 ]
[ 1366180-71-3 ]

Yield	Reaction Conditions	Operation in experiment
29%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 150℃; for 0.5h;Microwave irradiation;	General procedure: A solution of potassium carbonate (41.5 mg, 0.30 mmol) in water (0.5 mL) was added to a mixture of 2-(4-bromophenyl)-4-hydroxy-1,6-naphthyridine-3-carbonitrile (33 mg, 0.1 mmol) and the corresponding bromoaryl reagent (0.11 mmol) in a microwave vial, followed by addition of a solution of 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (6.5 mg, 8.9 mumol) in acetonitrile (0.5 mL). The mixture was heated by microwave for 30 min to 150C. The mixture was concentrated i. vac. The residue was dissolved in 1 mL of DMSO, filtered, and purified by HPLC. The reaction was conducted in 0.1 mmol scale unless indicated differently.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1944 - 1948

59
[ 1392268-11-9 ]
[ 90002-36-1 ]
[ 1392268-14-2 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 3278 - 3287

60
[ 491-38-3 ]
[ 90002-36-1 ]
[ 1283166-65-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7305 - 7312

61
[ 491-38-3 ]
[ 90002-36-1 ]
C₁₇H₁₆O₂ [ No CAS ]
[ 1283166-65-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7305 - 7312

62
[ 90002-36-1 ]
dimethyl (1-bromo-2-naphthyl)phosphonate [ No CAS ]
(+)-dimethyl 1-(2'-ethylphenyl)-2-naphthylphosphonate [ No CAS ]
(-)-dimethyl 1-(2'-ethylphenyl)-2-naphthylphosphonate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2395 - 2402

63
[ 1240662-56-9 ]
[ 90002-36-1 ]
(+)-diphenyl 1-(2'-ethylphenyl)-2-naphthylphosphonate [ No CAS ]
(+)-diethyl 1-(2'-ethylphenyl)-2-naphthylphosphonate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2395 - 2402

64
[ 90002-36-1 ]
[ 615-36-1 ]
[ 263901-49-1 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

65
[ 583-68-6 ]
[ 90002-36-1 ]
[ 1402547-20-9 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4
[2]Journal of the American Chemical Society,2017,vol. 139,p. 16210 - 16221

66
[ 90002-36-1 ]
[ 57946-63-1 ]
[ 1402547-23-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

67
[ 90002-36-1 ]
[ 1402547-25-4 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

68
[ 90002-36-1 ]
[ 1402547-28-7 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

69
[ 90002-36-1 ]
[ 1402547-31-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

70
[ 90002-36-1 ]
4-ethyl-9H-carbazole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4
[2]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

71
[ 90002-36-1 ]
[ 3955-65-5 ]
[ 16573-44-7 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4
[2]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

72
[ 90002-36-1 ]
[ 1402547-33-4 ]
[ 1402547-38-9 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

73
[ 90002-36-1 ]
[ 1402547-36-7 ]
[ 1402547-40-3 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

74
[ 90002-36-1 ]
[ 3955-65-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

75
[ 90002-36-1 ]
[ 1402547-38-9 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4
[2]Organic and biomolecular chemistry,2020,vol. 18,p. 3312 - 3323

76
[ 90002-36-1 ]
[ 1402547-40-3 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10487 - 10490,4

77
[ 1416332-54-1 ]
[ 90002-36-1 ]
[ 1416332-89-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 60 - 72

78
[ 1373433-13-6 ]
[ 90002-36-1 ]
[ 1400664-09-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In methanol; water; toluene; for 2h;Reflux;	General procedure: To a solution of 2-chloro-6-[3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenyl]-5H-pyrrolo[3,4-b]pyridin-7(6H)-one (70 mg, 0.18 mmol) and phenylboronic acid (44 mg, 0.36 mmol) in toluene and methanol (4:1, 5 ml) were added tetrakis(triphenylphosphine palladium (20 mg, 0.018 mmol) and sodium carbonate (0.18 ml, 0.54 mmol, 2M in H2O), then the mixture was refluxed for 2 h. After completion of reaction, the reaction mixture was combined with 20 ml of water and extracted with dichoromethane (20 ml x 2) being washed with water and brine. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was refined by silica gel column chromatography (10% MeOH/CH2Cl2) to give 52 mg (yield 67%) of the title compound.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1736 - 1739

79
[ 1426804-73-0 ]
[ 90002-36-1 ]
[ 1426802-84-7 ]

Yield	Reaction Conditions	Operation in experiment
78 mg	With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere; Microwave irradiation;	A mixture of <strong>[90002-36-1](2-ethylphenyl)boronic acid</strong> (77 mg), N-(4-bromo-3,5-difluorophenyl)-2-(4- (ethylsulfonyl)phenyl)acetamide (intermediate 27a, 120 mg), Pd2(dba)3 (26.3 mg), n-tert- butylphosphine, tetrafluoroboric acid salt (33.3 mg) and 2 M a2C03 (0.5 mL) in 1,4-dioxane (2 mL) was bubbled with N2, then sealed in the reaction vessel and heated in the microwave at 100C for 1 hour. After cooled to room temperature, the mixture was filtered tlirough celite, washed with EtOAc. The filtrate was washed with 2M HCl, sat. Na2C03 and brine, then concentrated in vacuo. The residue was purified by MDAP to afford N-(2'-ethyl-2,6-difluoro-[l,l '-biphenyl]-4-yl)-2-(4- (ethylsulfonyl)phenyl)acetarnide (78 mg) as a white solid. ?-NMR (400 MHz, DMSO- 6) delta ppm 1.03 (t, J= 7.6 Hz, 3H), 1.22 (t, J= 7.4 Hz, 3H), 2.44 (q, J= 7.6 Hz, 2H), 3.20 (q, J= 7.4 Hz, 2H), 3.86 (s, 2H), 7.11 (d, J= 7.5 Hz, 1H), 7.23 (m, 1H), 7.34 (m, 4H), 7.63 (d, J~ 8.3 Hz, 2H), 7.S9 (d, J = 8.3 Hz, 2H); 19F-NMR (376 MHz, DMSO-i/6) delta ppm -113.26; MS(ES") m/z 444 (MH+).

Reference： [1]Patent: WO2013/29338,2013,A1 .Location in patent: Page/Page column 120; 121

80
[ 290-37-9 ]
[ 90002-36-1 ]
[ 1425038-37-4 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 2639 - 2648

81
[ 90002-36-1 ]
[ 91026-00-5 ]
[ 1429862-79-2 ]
[ 1429862-73-6 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 3709 - 3719

82
[ 90002-36-1 ]
[ 1575-37-7 ]
[ 1430720-19-6 ]

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

83
[ 90002-36-1 ]
[ 1575-37-7 ]
[ 1430719-78-0 ]

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

84
[ 90002-36-1 ]
[ 108-88-3 ]
[ 101-81-5 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 7345 - 7353

85
[ 10323-39-4 ]
[ 90002-36-1 ]
[ 1609538-43-3 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 7662 - 7668

86
[ 38749-76-7 ]
[ 90002-36-1 ]
C₁₅H₁₇N [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 1243 - 1246

87
[ 38749-76-7 ]
[ 90002-36-1 ]
C₁₅H₁₅NO [ No CAS ]
C₁₅H₁₃NO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 1243 - 1246

88
[ 103858-52-2 ]
[ 90002-36-1 ]
ethyl 4-(2-ethylphenyl)-1H-indole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.9%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	Ethyl 4-bromo-1H-indole-2-carboxylate 9 (268.11 mg, 1.00 mmol, 1.0 eq), (2-ethylphenyl)boronic acid (224.97 mg, 1.50 mmol, 1.5 eq), Pd(PPh3)4 (57.79 mg, 0.05 mmol, 0.05 eq) and Na2CO3 (211.98 mg, 2.00 mmol, 2.0 eq) were dissolved in 15 mL of toluene, EtOH and H2O (10:3:2, v/v/v). The reaction mixture was purged with N2 and heated to reflux overnight. The reaction mixture was then filtered through Celite, washed with 20 mL H2O, dried with MgSO4, and purified by column chromatography (EtOAc:Heptane = 1:10, v/v) to afford ethyl 4-(2-ethylphenyl)-1H-indole-2-carboxylate 15. Yield: 92.9%. 1H NMR (400 MHz, Methanol-d4) delta 7.35 (d, J = 8.3 Hz, 1H), 7.29 - 7.18 (m, 3H), 7.17 - 7.07 (m, 2H), 6.84 (d, J = 6.8 Hz, 1H), 6.63 (s, 1H), 4.24 (q, J = 7.1 Hz, 2H), 2.39 (s, 2H), 1.26 (t, J = 7.1 Hz, 3H), 0.86 (t, J = 7.5 Hz, 3H).13C NMR (151 MHz, Methanol-d4) delta 162.0, 142.0, 139.5, 137.5, 135.8, 129.7, 128.2, 127.4, 127.3, 127.0, 125.0, 124.3, 120.4, 110.7, 107.2, 60.4, 26.0, 14.8, 13.2.

Reference： [1]Tetrahedron Letters,2020

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[ CAS No. 90002-36-1 ] {[proInfo.proName]}

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[ 90002-36-1 ] Synthesis Path-Upstream 1~3

[ 90002-36-1 ] Synthesis Path-Downstream 1~88

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Organoboron

Aryls

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[ 90002-36-1 ]