[ CAS No. 195062-62-5 ] {[proInfo.proName]}

Name: 195062-62-5|Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|95%
Brand: Ambeed
SKU: A284200
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Quality Control of [ 195062-62-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 195062-62-5 ]

SDS Specification

Alternatived Products of [ 195062-62-5 ]

Product Details of [ 195062-62-5 ]

CAS No. :	195062-62-5	MDL No. :	MFCD03453659
Formula :	C₁₅H₂₁BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NCVIYKCFTYSAGN-UHFFFAOYSA-N
M.W :	276.14	Pubchem ID :	2734618
Synonyms :

Calculated chemistry of [ 195062-62-5 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.53
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.0
TPSA :	44.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.13
Log Po/w (WLOGP) :	2.16
Log Po/w (MLOGP) :	1.79
Log Po/w (SILICOS-IT) :	2.16
Consensus Log Po/w :	1.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.091 mg/ml ; 0.00033 mol/l
Class :	Soluble
Log S (Ali) :	-3.74
Solubility :	0.0503 mg/ml ; 0.000182 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.48
Solubility :	0.00923 mg/ml ; 0.0000334 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.01

Safety of [ 195062-62-5 ]

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 [ 195062-62-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 195062-62-5 ]
Downstream synthetic route of [ 195062-62-5 ]

[ 195062-62-5 ] Synthesis Path-Upstream 1~2

1
[ 195062-62-5 ]
[ 1667-12-5 ]

Reference： [1] Archives of Pharmacal Research, 2010, vol. 33, # 12, p. 1919 - 1926

2
[ 93-89-0 ]
[ 25015-63-8 ]
[ 195062-62-5 ]
[ 269409-99-6 ]
[ 269410-00-6 ]

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 51, p. 12868 - 12869
[2] Journal of the American Chemical Society, 2000, vol. 122, # 51, p. 12868 - 12869

[ 195062-62-5 ] Synthesis Path-Downstream 1~88

1
[ 10385-36-1 ]
[ 195062-62-5 ]
[ 934176-70-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1101 - 1115

2
[ 862728-61-8 ]
[ 195062-62-5 ]
4-(4-amino-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18.1%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux;	3-Bromo-l -/er/-butyl-lH-pyrazolo[3,4-d]pyrimidin-4-ylamine (351 mg, 1.3 mmol), ethyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (395 mg, 1.43 mmol), tetrakistriphenylphosphine palladium (90 mg, 0.07 mmol) and sodium carbonate (330 mg, 3.11 mmol) were mixed in 1,2-dimethoxyethane (20 ml) and water (10 ml) and the solution refluxed under argon for 6 hr. Water was added and the product was extracted with ethyl acetate (3 x 25 ml). Evaporation of the solvent followed by flash chromatography on silica gel (eluent, hexanerethyl acetate, 80:20 to 60:40) afforded the title compound that was crystallized form methanol (80 mg, 18.1 %); LC/MS, API-ES, Pos, (M+H)+, 340.1.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux;	3-Bromo-l-fert-butyl-lH-pyrazolo[3,4-d]pyrimidin-4-ylamine (351 mg, 1.3 mmol), ethyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (395 mg, 1.43 mmol), tetrakistriphenylphosphine palladium (90 mg, 0.07 mmol) and sodium carbonate (330 mg, 3.11 mmol) were mixed in 1,2-dimethoxyethane (20 ml) and water (10 ml) and the solution refluxed under argon for 6 hr. Water was added and the product was extracted with ethyl acetate (3 x 25 ml). Evaporation of the solvent followed by flash chromatography on silica gel (eluent, hexane:ethyl acetate, 80:20 to 60:40) afforded the title compound that was crystallized form methanol (80 mg, 0.24 mmol); LC/MS, API-ES, Pos, (M+H)+, 340.1.

Reference： [1]Patent: WO2007/126841,2007,A2 .Location in patent: Page/Page column 82-83
[2]Patent: WO2009/62118,2009,A2 .Location in patent: Page/Page column 180-181

3
[ 7335-27-5 ]
[ 25015-63-8 ]
[ 93-89-0 ]
[ 195062-62-5 ]

Reference： [1]Synlett,2006,p. 1867 - 1870
[2]Heterocycles,2010,vol. 80,p. 213 - 218
[3]Heterocycles,2010,vol. 80,p. 213 - 218

4
[ 871030-89-6 ]
[ 76-09-5 ]
[ 195062-62-5 ]

Reference： [1]Chemical Communications,2007,p. 3667 - 3669

5
[ 195062-62-5 ]
2',3',4'-trimethoxy-biphenyl-4-carbonyl chloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1101 - 1115

6
[ 195062-62-5 ]
[ 132491-64-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1101 - 1115

7
[ 195062-62-5 ]
[ 934176-71-3 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1101 - 1115

8
[ 195062-62-5 ]
[ 934176-72-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1101 - 1115

9
[ 195062-62-5 ]
(5-{2-[(2',3',4'-trihydroxy-biphenyl-4-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1101 - 1115

Yield	Reaction Conditions	Operation in experiment
67%	With p-phenylpyridine; potassium methanolate; In tert-butyl methyl ether; at 85℃; for 12h;	General procedure: According to the method described in Scheme 1) above,It is possible to synthesize aryl borates with different aromatic ring substituents (as shown in Table 1).The resulting aryl borates are known compounds, and their characterization data are consistent with those reported in the literature.
50%		General procedure: Under an argon atmosphere, potassium methoxide (KOMe)(Manufactured by ALDRICH) 42.1 mg (0.6 mmol),5 ml of 1,2-dimethoxyethane (DME)And 196.7 mg (0.75 mmol) of (dimethylphenylsilyl) boronic acid pinacol ester (manufactured by ALDRICH) were added,And the mixture was stirred at 30 C. for 10 minutes.after that,4-bromoanisole (manufactured by Wako Pure Chemical Industries, Ltd.)93.5 mg (0.50 mmol) was added dropwise and reaction was carried out for 1 hour,The reaction mixture was analyzed using gas chromatography (GC)It was confirmed whether the reaction was completed.After the reaction, it was cooled to 0 C., tetrabutylammonium fluoride(TBAF) (1.0 M, 800 mul), and the mixture was stirred for 3 hours.Thereafter, 100 ml of water was added to the mixed solution,Subsequently, the target product was extracted with 50 ml of diethyl ether.The organic layer was washed twice with 50 ml of water,Magnesium sulfate was added and dried. After filtering magnesium sulfate,Diethyl ether of the filtrate was distilled off.The obtained crudeThe product was purified with 0-5% hexane / diethyl ether eluent using boron impregnated silica gel column chromatography,To give 4-methoxyphenylboronic acid pinacol ester as a colorless oil. The yield calculated from GC was 92%The yield upon isolation was 77%.

11
[ 760989-17-1 ]
[ 195062-62-5 ]
ethyl 4-(6-[(trans-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 85℃;	To A degassed suspension of Example 1C (trans, 45.0 mg, 0.110 mmol) in DME/ETOH/H2O (7: 3: 2) were added 4- (4, 4,5, 5-TETRAMETHYL- [1, 3, 2] dioxaborolan-2-yl) -benzoic acid ethyl ester (31. 8 RL, 0.121 MMOL), NA2CO3 (1M, 0.11 ML), AND PD (PPh3) 2Cl2 (7.7 mg, 0. 0110 mmol). The reaction mixture was heated overnight at 85 C in a sealed vial. The mixture was concentrated and the residue was extracted with EtOAc, washed with brine, dried over MGSO4, filtered, and concentrated. The residue was purified using preparative HPLC (see condition in Example 1D) to give 8.8 mg (12%) of the desired product as white foam. MS (DCI/NH3) m/z: 430.2 (M+H) + ; 'H NMR (300 MHz, CD30D) 8 0.95 (d, J=6. 78 Hz, 3 H), 1.09 (m, 2 H), 1.42 (t, J=7. 12 Hz, 3 H), 1.42-1. 57 (m, 3 H), 1.82-1. 94 (m, 2 H), 2.16-2. 29 (m, 2 H), 3.15 (m, 1 H), 3.98 (s, 2 H), 4.30 (s, 2 H), 4.40 (q, J=7.12 Hz, 2 H), 7.52 (d, J=7.80 Hz, 1 H), 7.72 (s, 1 H), 7.82 (d, J=7. 80 Hz, 1 H), 7.92 (d, J=8. 82 Hz, 2 H), 8. 15 (d, J=8.48 Hz, 2 H).

Reference： [1]Patent: WO2004/80973,2004,A1 .Location in patent: Page 47

12
[ 619-44-3 ]
[ 25015-63-8 ]
[ 195062-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 85℃; for 16h;	EXAMPLE 13 Preparation of Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Benzoate; [0105] EMI310.0[0106] A solution of methyl 4-iodobenzoate (2.00 g, 7.63 mmol) in 30 mL dioxane was degassed with Ar for 10 minutes. Then, Pd(dppf)Cl2 (171 mg, 3 mol %), triethylamine (3.27 mL), and pinacolborane (1.47 g, 11.45 mmol) were added. The resulting solution was stirred at 85[deg.] C. for 16 hours. The mixture was allowed to cool to ambient temperature, filtered through a pad of Celite(R), and concentrated in vacuo to obtain 3.97 g of product which was used without further purification. m/z=263 [M+H]<+>.

Reference： [1]Patent: US2003/195352,2003,A1 .Location in patent: Page/Page column 34

13
[ 362707-80-0 ]
[ 195062-62-5 ]
3'-(3,4,8,9-tetrahydro-6-methoxy-3,3,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)[1,1'-biphenyl]-4-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In 1,2-dimethoxyethane; ethanol; water;	3'-(3,4,8,9-Tetrahydro-6-methoxy-3,3,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)[1.1'-biphenyl]-4-carboxylic acid ethyl ester A suspension of 1-(3-bromophenyl)-3,4,8,9-tetrahydro-6-methoxy-3,3,8,8-tetramethylfuro[2,3-h]isoquinoline (2.81 g, 6.78 mmol), <strong>[195062-62-5]4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid ethyl ester</strong> (2.25 g, 8.15 mmol), sodium carbonate (1.08 g, 10.2 mmol) and tetrakis(triphenylphosphine)palladium (0) (157 mg, 0.136 mmol) in 1,2-dimethoxyethane (24 mL), ethanol (12 mL) and water (12 mL) was stirred at 80 C for 14 hours under nitrogen atmosphere. The reaction mixture was combined with water and extracted twice with ethyl acetate. The combined organic layer was washed with water and brine, dried through sodium sulfate-basic silica gel (eluding with ethyl acetate), and concentrated under reduced pressure. The residue was subjected to a column chromatography on a basic silica gel (hexane/ethyl acetate, 10:1) to obtain the title compound (2.87g, yield: 88%). Amorphous. 1H NMR (CDCl3) delta 1.27 (6H, s), 1.30 (6H, s), 1.42 (3H, t, J = 7.1 Hz), 2.26 (2H, s), 2.72 (2H, s), 3.93 (3H, s), 4.40 (2H, q, J = 7.1 Hz), 6.63 (1H, s), 7.37-7.54 (2H, m), 7.62-7.71 (4H, m), 8.10 (2H, d, J = 8.4 Hz).

Reference： [1]Patent: EP1270577,2003,A1

14
[ 362715-87-5 ]
[ 195062-62-5 ]
3'-(6-hydroxy-4,4,8,8-tetramethyl-3,4,8,9-tetrahydrofuro[2,3-h]isoquinolin-1-yl)[1,1'-biphenyl]-4-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		3'-(6-Hydroxy-4,4,8,8-tetramethyl-3,4,8,9-tetrahydrofuro[2,3-h]isoquinolin-1-yl)[1,1'-biphenyl]-4-carboxylic acid ethyl ester The title compound was obtained from 1-(3-bromophenyl)-3,4,8,9-tetrahydro-4,4,8,8-tetramethyl-6-furo[2,3-h]isoquinolinol and <strong>[195062-62-5]4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid ethyl ester</strong> by the method similar to that in EXAMPLE 461. Yield: 52%. Melting point: 214-217 C (ethyl acetate-diethyl ether). 1H NMR (CDCl3) delta 1.21 (6H, s), 1.28 (6H, s), 1.41 (3H, t, J = 7.2 Hz), 2.32 (2H, s), 3.60 (2H, s), 4.40 (2H, q, J = 7.2 Hz), 6.73 (1H, s), 7.38-7.54 (2H, m), 7.63-7.77 (2H, m), 7.68 (2H, d, J = 8.4 Hz), 8.09 (2H, d, J = 8.4 Hz).

Reference： [1]Patent: EP1270577,2003,A1

15
[ 76-09-5 ]
[ 5798-75-4 ]
[ 51901-85-0 ]
[ 7440-66-6 ]
[ 195062-62-5 ]

Reference： [1]Chemical Communications,2007,p. 3667 - 3669

16
[ 76-09-5 ]
[ 51934-41-9 ]
[ 51901-85-0 ]
[ 7440-66-6 ]
[ 195062-62-5 ]

Reference： [1]Chemical Communications,2007,p. 3667 - 3669

17
[ 591-50-4 ]
[ 195062-62-5 ]
[ 6301-56-0 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1846 - 1849

18
[ 94-09-7 ]
[ 73183-34-3 ]
[ 195062-62-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tert.-butylnitrite; dibenzoyl peroxide; In acetonitrile; at 20℃; for 4h;	EXAMPLE 4 Synthesis of ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate B2pin2 (1.0 mmol, 254 mg), benzoyl peroxide (0.02 mmol, 5 mg), ethyl 4-aminobenzoate (1 mmol, 165 mg) and acetonitrile (3 mL) were added in a 25 mL tube-type reactor, followed by the addition of tert-butyl nitrite (1.5 mmol, 154 mg). The reaction was conducted at room temperature for 4 h. The solution was concentrated after the reaction and the resultant was purified by column chromatography (eluted by petroleum ether:ethyl acetate=20:1, V:V) to give ethyl 4-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate having the following structure: This compound is pale yellow liquid and obtained in 79% yield. Its NMR data are as follows: 1H NMR (400 MHz, CDCl3) delta 8.02 (d, 2H, J=8.4 Hz), 7.87 (d, 2H, J=8.4 Hz), 4.38 (q, 1H, J=7.1 Hz), 1.42~1.35(m, 15H); 13C NMR (100 MHz, CDCl3) delta 166.6, 134.5, 132.6, 128.5, 84.1, 61.0, 24.8, 14.2.
79%	With tert.-butylnitrite; dibenzoyl peroxide; In acetonitrile; at 20℃; for 4h;	B2pin2 (1.0 mmol, 254 mg), benzoyl peroxide (0.02 mmol, 5 mg), ethyl 4-aminobenzoate (1 mmol, 165 mg) and acetonitrile (3 mL) were added in a 25 mL tube-type reactor, followed by the addition of tert-butyl nitrite (1.5 mmol, 154 mg). The reaction was conducted at room temperature for 4 h. The solution was concentrated after the reaction and the resultant was purified by column chromatography (eluted by petroleum ether : ethyl acetate = 20:1, V:V) to give ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate having the following structure: This compound is pale yellow liquid and obtained in 79% yield. Its NMR data are as follows: 1H NMR (400MHz, CDCl3) delta 8.02 (d, 2H, J=8.4Hz), 7.87 (d, 2H, J=8.4Hz), 4.38 (q, 1H, J=7.1Hz), 1.42~1.35(m, 15H); 13C NMR (100MHz, CDCl3) delta 166.6, 134.5, 132.6, 128.5, 84.1, 61.0, 24.8, 14.2.
77%		General procedure: An arylamine (50 mmol) was dissolved in 50% hydrofluoroboric acid(17 mL) and water (20 mL). After cooling the reaction mixture to 0 C, asolution of sodium nitrite (3.4 g in 7.5 mL water) was added dropwise tothe reaction system (over 5 min). The resulting mixture was stirred for 1h and the precipitate was collected by filtration. It was redissolved in theminimum amount of acetone and then diethyl ether was added to precipitatethe aryl diazonium tetrafluoroborate. The product was filtered, washedwith diethyl ether and dried under reduced pressure.Borylation of aryldiazonium salts; general procedureThe aryldiazonium salt (0.5 mmol) and (Bpin)2 (0.75 mmol) were added toan oven-dried Schlenk tube. The tube was evacuated and backfilled with argon (three times). CH3OH (0.8 mL) was added to this Schlenk tube.The tube was sealed and the mixture was stirred at room temperature(22-25 C) for 36 h. After evaporation of the solvent, the residue waspurified by column chromatography to afford the product.The arylboronates were purified by chromatography on a silica column eluting with petroleum ether (boiling range 60-90 C) or a petroleumether/ethyl acetate mixture (ca. 60:1) by volume giving Rf values for theboronates of ca. 0.2-0.3.

75%

General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv) followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg of NaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0-5 C followed by B2pin2 (2, 381 mg, 1.5 mmol, 3.0equiv) in MeOH (1.0 mL). This mixture was stirred 60 min.H2O (10 mL) was added to the reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layers were washed with sat. NaHCO3, dried over Na2SO4, followed by evaporation, and the crude residue was purified by flash chromatography.

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1846 - 1849
[2]Angewandte Chemie - International Edition,2010,vol. 49,p. 1846 - 1849
[3]Patent: US2012/184768,2012,A1 .Location in patent: Page/Page column 3
[4]Patent: EP2481742,2012,A1 .Location in patent: Page/Page column 4-5
[5]Journal of Chemical Research,2018,vol. 42,p. 481 - 485
[6]Synlett,2014,vol. 25,p. 1577 - 1584

19
3-(4-phenylbut-1-yn-1-yl)-1,3-oxazolidin-2-one [ No CAS ]
[ 195062-62-5 ]
C₂₂H₂₃NO₄ [ No CAS ]
[ 1245223-33-9 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 6026 - 6031

20
[ 2404-35-5 ]
[ 195062-62-5 ]
[ 1239573-01-3 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 10674 - 10676

21
[ 925-90-6 ]
[ 195062-62-5 ]
MgBr[(p-(ethoxycarbonyl)phenyl)(ethyl)B((pinacol)(-2H))] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 10674 - 10676

22
[ 120-47-8 ]
[ 195062-62-5 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 6913 - 6917
[2]Journal of the American Chemical Society,2015,vol. 137,p. 1593 - 1600

23
[ 98634-20-9 ]
[ 73183-34-3 ]
[ 195062-62-5 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 6913 - 6917

24
[ 14348-75-5 ]
[ 195062-62-5 ]
[ 1313187-37-9 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 5729 - 5733

25
[ 14348-75-5 ]
[ 195062-62-5 ]
[ 1313187-44-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 5729 - 5733

26
[ 145294-78-6 ]
[ 195062-62-5 ]
[ 1333419-35-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7333 - 7336

27
[ 1286990-00-8 ]
[ 25015-63-8 ]
[ 195062-62-5 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 962 - 963
[2]Chemistry Letters,2011,vol. 40,p. 962 - 963
[3]Chemistry Letters,2011,vol. 40,p. 962 - 963
[4]Chemistry Letters,2011,vol. 40,p. 962 - 963
[5]Chemistry Letters,2011,vol. 40,p. 962 - 963

28
[ 5798-75-4 ]
[ 73183-34-3 ]
[ 195062-62-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 140℃; for 0.333333h;Sealed tube;	INTERMEDIATE 116: ethyl 4-(5-((((R)-2-((R)-1-(N- (benzyloxy)formamido)propy moyl)furan-2-yl)benzoate Step 1 : ethyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate Ethyl 4-bromobenzoate (0.356 mL, 2.183 mmol), bis(pinacolato)diboron (0.665 g, 2.62 mmol), potassium acetate (0.857 g, 8.73 mmol), PdCI2(dppf)-CH2CI2 (0.089 g, 0.109 mmol) in 1 ,4-dioxane (20 mL) was placed in a microwave vial. The vial was sealed and heated to 140 C for 20 min in iwave. The reaction was diluted with EtOAc (100 mL) and brine (100 mL) and passed through a pad of celite. The organic phase was passed through a phase separator and the organic phase was concentrated. Purification by Si (0-100% EtOAc/Hex) afforded the title compound as a yellow oil. (876 mg, 67 % yield). MS (m/z) 277.2 (M+H)+

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 2087 - 2092
[2]Journal of the American Chemical Society,2020
[3]Chemical Science,2016,vol. 7,p. 3676 - 3680
[4]Inorganic Chemistry,2016,vol. 55,p. 8871 - 8880
[5]Journal of the American Chemical Society,2017,vol. 139,p. 7745 - 7748
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Angew. Chem.,2018,p. 11165 - 11169,5
[8]Archives of Pharmacal Research,2010,vol. 33,p. 1919 - 1926
[9]ChemCatChem,2016,vol. 8,p. 2317 - 2320

29
[ 5798-75-4 ]
[ 195062-62-5 ]
[ 47230-38-6 ]