[ CAS No. 882679-40-5 ] {[proInfo.proName]}

Name: 882679-40-5|Methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|95%
Brand: Ambeed
SKU: A101989
Price: 5.0 USD
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Quality Control of [ 882679-40-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 882679-40-5 ]

SDS Specification

Alternatived Products of [ 882679-40-5 ]

Product Details of [ 882679-40-5 ]

CAS No. :	882679-40-5	MDL No. :	MFCD11520530
Formula :	C₁₅H₂₁BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HAPIXNBOBZHNCA-UHFFFAOYSA-N
M.W :	276.14	Pubchem ID :	53217136
Synonyms :

Calculated chemistry of [ 882679-40-5 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.53
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.16
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) :	2.08
Log Po/w (MLOGP) :	1.79
Log Po/w (SILICOS-IT) :	2.29
Consensus Log Po/w :	1.86

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.55
Solubility :	0.0782 mg/ml ; 0.000283 mol/l
Class :	Soluble
Log S (Ali) :	-3.74
Solubility :	0.0503 mg/ml ; 0.000182 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.46
Solubility :	0.0096 mg/ml ; 0.0000348 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.22

Safety of [ 882679-40-5 ]

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

Application In Synthesis of [ 882679-40-5 ]

* 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 [ 882679-40-5 ]
Downstream synthetic route of [ 882679-40-5 ]

[ 882679-40-5 ] Synthesis Path-Upstream 1~8

1
[ 104901-43-1 ]
[ 73183-34-3 ]
[ 882679-40-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 16 h; Inert atmosphere	Methyl 3-bromo-4-methylbenzoate (3 mL, 19.2 mmol) was dissolved in 1,4-dioxane (96 mL), and bis(pinacolato)diboron (7.31 g, 28.2 mmol), potassium acetate (5.65 g, 57.6 mmol), and Pd(dppf)Cl₂ (2.8 g, 3.84 mmol) were added thereto. The resulting mixture was replaced with argon, and stirred at 90°C for 16 hours. The mixture was cooled to room temperature, and water was added. Then, the mixture was extracted with EtOAc. An organic layer was dried over magnesium sulfate, concentrated, and then purified using silica gel chromatography to obtain the title compound (off-white solid, 4.46 g, and 84percent yield). ¹H NMR (300 MHz, CDCl₃) δ 8.40 (d, 1H), 7.97 (dd, 1H), 7.23 (d, 1H), 3.94-3.87 (m, 3H), 2.58 (s, 3H), 1.35 (d, 12H).

Reference： [1] Chemical Communications, 2012, vol. 48, # 34, p. 4115 - 4117
[2] Patent: EP2963027, 2016, A1, . Location in patent: Paragraph 0470; 0471; 0472
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4869 - 4881

2
[ 90347-66-3 ]
[ 73183-34-3 ]
[ 882679-40-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere	Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4',4',5,5,5',5^,-octamethyl-2,2'-bi(l ,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCl₂(dppf CH₂Cl₂ (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 °C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous NaHC0₃ (80 mL), brine (80 mL), dried (MgS0₄), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71 percent). NMR (400 MHz, CDC1₃) 5 8.41 (d, J = 1.9 Hz, 1 H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere	Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCi₂(dppf CH₂Ci2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 °C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous aHC03 (80 mL), brine (80 mL), dried (MgS0₄), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71percent). NMR (400 MHz, CDC1₃) δ 8.41 (d, J= 1.9 Hz, 1H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58 (s, 3H), 1.35 (s, 12H).

Reference： [1] Patent: WO2014/8197, 2014, A1, . Location in patent: Page/Page column 71; 72
[2] Patent: WO2015/95767, 2015, A1, . Location in patent: Page/Page column 86

3
[ 99-75-2 ]
[ 73183-34-3 ]
[ 882679-40-5 ]

Yield	Reaction Conditions	Operation in experiment
59%	at 120℃; for 36 h; Sealed tube; Inert atmosphere	Pt(SIPr)(dvtms) (6.9 mg, 9.0 mol), B2pin2 (91 mg, 0.36 mmol), methyl 4-methylbenzoate (49mg, 0.30 mmol) and 1,3,5-triisopropylbenzene (0.10 mL) were added to a 10 mL-sample vial witha Teflon-sealed screwcap. The cap was applied to seal the vial under the flow of N2. The mixturewas stirred at 120 °C for 20 h and the resulting mixture was filtered through a pad of silica gel(eluting with 7 mL of hexane/EtOAc = 5/1). The filtrate was concentrated in vacuo and purifiedby flash column chromatography over silica gel (eluting with hexane/AcOEt = 100/1 to 50/1) togive the target borylated product as a white solid (35 mg, 42percent) and 26 mg of unreacted startingmaterial was recovered (52percent). The recovered starting material was transferred to another vial forrepeating the borylation. Pt(SIPr)(dvtms) (4.9 mg, 6.4 mol), B2pin2 (51 mg, 0.20 mmol) and1,3,5-triisopropylbenzen (0.1 mL) were added. The mixture was stirred at 120 °C for 16 h and theresulting mixture was filtered through a pad of silica gel (eluting with 7 mL of hexane/AcOEt =5/1). The filtrate was concentrated in vacuo and purified by flash column chromatography to givethe target borylated product (14 mg, 17percent based on starting arene) and 7.9 mg of unreacted startingmaterial was recovered. As a result of two borylation, 59percent of the target product was obtained and16percent of unreacted starting was recovered.Rf 0.49 (hexane/EtOAc = 5/1). White solid (49 mg, 59percent).

Reference： [1] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 332 - 342

4
[ 876189-18-3 ]
[ 76-09-5 ]
[ 882679-40-5 ]

Reference： [1] Patent: WO2014/144380, 2014, A1, . Location in patent: Page/Page column 110

5
[ 1350764-46-3 ]
[ 25015-63-8 ]
[ 882679-40-5 ]

Reference： [1] Chemistry Letters, 2011, vol. 40, # 9, p. 962 - 963
[2] Chemistry Letters, 2011, vol. 40, # 9, p. 962 - 963

6
[ 82998-57-0 ]
[ 882679-40-5 ]

Reference： [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,

7
[ 7697-26-9 ]
[ 882679-40-5 ]

Reference： [1] Patent: WO2014/144380, 2014, A1,

8
[ 170230-88-3 ]
[ 882679-40-5 ]

Reference： [1] Patent: WO2014/144380, 2014, A1,

[ 882679-40-5 ] Synthesis Path-Downstream 1~88

2
[ 1350764-46-3 ]
[ 25015-63-8 ]
[ 882679-40-5 ]

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

3
[ 882679-40-5 ]
[ 1333264-35-9 ]

Reference： [1]Patent: WO2011/109277,2011,A1

4
[ 882679-40-5 ]
[ 1333264-34-8 ]

Reference： [1]Patent: WO2011/109277,2011,A1

5
[ 882679-40-5 ]
[ 1333264-78-0 ]

Reference： [1]Patent: WO2011/109277,2011,A1

6
[ 882679-40-5 ]
[ 1333264-79-1 ]

Reference： [1]Patent: WO2011/109277,2011,A1

7
[ 882679-40-5 ]
[ 1333264-77-9 ]

Reference： [1]Patent: WO2011/109277,2011,A1

8
[ 882679-40-5 ]
[ 1333263-97-0 ]
[ 1333264-27-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl;palladium diacetate; In tetrahydrofuran; water; at 75℃; for 14h;	5-chloro-l -[(2,2-difluorocyclopropyl)methyl]-3-methyl- 1 ,3-dihydro[ 1 ,2,5] thiadiazolo[3,4-b]pyridine 2,2-dioxide (29-1) (6.6 g, 21.3 mmol, 1.0 eq), methyl 4-methyl-3- (4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)benzoate (8.8 g, 32.0 mmol, 1.5 eq), tripotassium phosphate (9.0 g, 42.6 mmol, 2.0 eq), S-Phos (875 mg, 2.1 mmol, 0.1 eq), and palladium(II) acetate (239 mg, 1.1 mmol, 0.05 eq) were combined in THF (90 mL) and water (15 mL). The resulting mixture was heated at 75 C for 14 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (300 mL), washed with water (100 mL) and brine (100 mL), dried over MgS04, filtered and concentrated. The crude residue was purified by flash chromatography (330 g Si02, 0-60% EtOAc in hexanes) to afford methyl 3-{l- [(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4- b]pyridin-5-yl}-4-methylbenzoate (38-1) as a yellow solid. HRMS m/z (M+H) 424.1135 found, 424.1137 required.

Reference： [1]Patent: WO2011/109277,2011,A1 .Location in patent: Page/Page column 88

9
[ 882679-40-5 ]
[ 1221343-14-1 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 4115 - 4117
[2]Patent: WO2014/144380,2014,A1

10
[ 104901-43-1 ]
[ 73183-34-3 ]
[ 882679-40-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere;	Methyl 3-bromo-4-methylbenzoate (3 mL, 19.2 mmol) was dissolved in 1,4-dioxane (96 mL), and bis(pinacolato)diboron (7.31 g, 28.2 mmol), potassium acetate (5.65 g, 57.6 mmol), and Pd(dppf)Cl2 (2.8 g, 3.84 mmol) were added thereto. The resulting mixture was replaced with argon, and stirred at 90C for 16 hours. The mixture was cooled to room temperature, and water was added. Then, the mixture was extracted with EtOAc. An organic layer was dried over magnesium sulfate, concentrated, and then purified using silica gel chromatography to obtain the title compound (off-white solid, 4.46 g, and 84% yield). 1H NMR (300 MHz, CDCl3) delta 8.40 (d, 1H), 7.97 (dd, 1H), 7.23 (d, 1H), 3.94-3.87 (m, 3H), 2.58 (s, 3H), 1.35 (d, 12H).

Reference： [1]Chemical Communications,2012,vol. 48,p. 4115 - 4117
[2]Patent: EP2963027,2016,A1 .Location in patent: Paragraph 0470; 0471; 0472
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 4869 - 4881

11
[ 353-83-3 ]
[ 882679-40-5 ]
[ 1393479-22-5 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 8273 - 8275

12
[ 882679-40-5 ]
[ 1459216-63-7 ]
[ 1459216-73-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 120℃; for 0.5h;Microwave irradiation;	A mixture of (R)-6-bromo-N2-(1-(4-chlorophenyl)ethyl)pyrazine-2,3-diamine (325 mg, 1.0mmol), <strong>[882679-40-5]methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate</strong> (357 mg, 1.3mmol), Pd(dppf)Cl2 (73 mg, 0.1 mmol), and Cs2CO3 (650 mg, 2 mmol) in 1,4-dioxane (3.0 mL)and H2O (1.0 mL) was heated under microwave irradiation at 120 C for 30 min. The solid was removed via filtration and the solution was partitioned between H2O (5 mL) and EtOAc (20 mL).The EtOAc layer was concentrated and purified by column chromatography (50% EtOAc inpetroleum ether) and provided the title compound (340 mg, 86% yield).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5533 - 5539

13
[ 882679-40-5 ]
[ 16265-11-5 ]
[ 1533440-46-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere;	Compound 7.1. Methyl 4-methyl-3-(2-methyl-lH-imidazol-5-yl)benzoate. To a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 600 mg, 2.17 mmol) in dioxane (20 mL) was added 2-methyl-4-bromo imidazole (419 mg, 2.6 mmol), Pd(dppi)Cl2*CH2Cl2 (180 mg, 0.22 mmol). The mixture was degassed argon and stirred for 10 minutes then aqueous potassium carbonate (1M, 10 mL, 10 mmol) was added and the mixture was stirred at 90 C for 18 h. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and filtered through Celite. The organic phase was washed by brine, dried (MgSC>4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5 % MeOH in EtOAc) to yield the title compound as a foam (324 mg, 65%). m/z (ES+) 231 (M+H)+. NMR (400 MHz, CDC13) delta 8.30 (br s, 1H), 7.86 (dd, J= 7.9, 1.9 Hz, 1H), 7.32 (d, J= 7.9 Hz, 1

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 77

14
[ 4522-35-4 ]
[ 882679-40-5 ]
[ 1533442-82-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere;	Compound 51.1. Methyl 4-methyl-3-(lH-pyrazoI-5-yl)benzoate. To methyl 4- methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-lH-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2 FontWeight="Bold" FontSize="10" DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90 C for 18 h, then cooled and diluted with EtOAc and filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02; 0-30 % EtOAc in hexanes) to yield 258 mg (41 %) of the title compound as a solid. m/z
41%		Compound 51.1. Methyl 4-methyl-3-(lH-pyrazol-5-yl)benzoate. To methyl 4- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-lH-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2 DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90 C for 18 h, then cooled and diluted with EtOAc and filtered through Celite. The filtrate was washed with brine, dried (MgSC^), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (S1O2; (M0-30 % EtOAc in hexanes) to yield 258 mg (41 %) of the title compound as a solid, m/z (ES+) 217 (M-H)+

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 120
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 135; 136

15
[ 90347-66-3 ]
[ 73183-34-3 ]
[ 882679-40-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃;Inert atmosphere;	Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4',4',5,5,5',5,-octamethyl-2,2'-bi(l ,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCl2(dppf CH2Cl2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous NaHC03 (80 mL), brine (80 mL), dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71 %). NMR (400 MHz, CDC13) 5 8.41 (d, J = 1.9 Hz, 1 H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃;Inert atmosphere;	Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCi2(dppf CH2Ci2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous aHC03 (80 mL), brine (80 mL), dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71%). NMR (400 MHz, CDC13) delta 8.41 (d, J= 1.9 Hz, 1H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58 (s, 3H), 1.35 (s, 12H).

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 71; 72
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 86

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[ 82998-57-0 ]
[ 882679-40-5 ]

Reference： [1]Patent: WO2014/8197,2014,A1
[2]Patent: WO2015/95767,2015,A1

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[ 882679-40-5 ]
[ 1533440-47-9 ]

Reference： [1]Patent: WO2014/8197,2014,A1

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[ 882679-40-5 ]
[ 1533440-48-0 ]

Reference： [1]Patent: WO2014/8197,2014,A1

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[ 882679-40-5 ]
[ 1533435-87-8 ]

Reference： [1]Patent: WO2014/8197,2014,A1
[2]Patent: WO2015/95767,2015,A1

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[ 882679-40-5 ]
[ 1533440-61-7 ]

Reference： [1]Patent: WO2014/8197,2014,A1

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[ 882679-40-5 ]
[ 1533440-79-7 ]

Reference： [1]Patent: WO2014/8197,2014,A1
[2]Patent: WO2015/95767,2015,A1

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[ 882679-40-5 ]
[ 1533440-80-0 ]

Reference： [1]Patent: WO2014/8197,2014,A1
[2]Patent: WO2015/95767,2015,A1

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[ 882679-40-5 ]
[ 1533440-44-6 ]

Reference： [1]Patent: WO2014/8197,2014,A1

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[ 882679-40-5 ]
[ 1533435-85-6 ]

Reference： [1]Patent: WO2014/8197,2014,A1

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[ 631897-38-6 ]
[ 882679-40-5 ]
[ 1533440-43-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 26h;Inert atmosphere;	Compound 5.6. Methyl 3-(2,4-dimethyl-lH-imidazol-5-yl)-4-methylbenzoate. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 3.56 g, 12.9 mmol), 5-iodo-2,4-dimethyl-lH-imidazole (compound 5.5, 3.43 g, 15.4 mmol), K2C03 (5.33 g, 38.6 mmol) and PdCl2(dppf CH2Cl2 (1.05 g, 1.29 mmol) were added to a round bottom flask. The flask was purged with argon, then dioxane (70 mL) and water (20 mL) were added and the mixture was heated at 90 C for 16 hours. The mixture was cooled then additional K2C03 (1M, 25 mL, 25.0 mmol) and catalyst PdCl2(dppf CH2Cl2 (l .Og, 1.2 mmol) were added. The mixture was heated at 90 C for an additional 10 hours, then cooled to room temperature and filtered through Celite. The solvent was removed under reduced pressure and the residue was cooled to 0 C and acidified to pH 3-4 with aqueous HCl (2 M). The acidic mixture was washed with EtOAc (150 mL) and then the aqueous material was adjusted to pH 10-1 1 with aqueous sodium hydroxide (2 M) and extracted with EtOAc (5 x 200 mL). The combined organic phases were dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (DCM to 5% MeOH in DCM) to yield the title compound as a thick brown oil (2.42 g, 77%). m/z (ES+) 245(M+H)+. NMR (400 MHz, CDC13) delta 7.89-7.87 (m, 2H), 7.31 (d with fine str, J= 8.6 Hz, 1 H
77%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 26h;Inert atmosphere;	Compound 5.6. Methyl 3-(2,4-dimethyl-lH-imidazol-5-yl)-4-methylbenzoate. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 3.56 g, 12.9 mmol), 5 -iodo-2,4-dimethyl-lH- imidazole (compound 5.5, 3.43 g, 15.4 mmol), K2C03 (5.33 g, 38.6 mmol) and PdCl2(dppf CH2Cl2 (1.05 g, 1.29 mmol) were added to a round bottom flask. The flask was purged with argon, then dioxane (70 mL) and water (20 mL) were added and the mixture was heated at 90 C for 16 hours. The mixture was cooled then additional K2C03 (1M, 25 mL, 25.0 mmol) and catalyst PdCl2(dppf CH2Cl2 (l.Og, 1.2 mmol) were added. The mixture was heated at 90 C for an additional 10 hours, then cooled to room temperature and filtered through Celite. The solvent was removed under reduced pressure and the residue was cooled to 0 C and acidified to pH 3-4 with aqueous HCl (2 M). The acidic mixture was washed with EtOAc (150 mL) and then the aqueous material was adjusted to pH 10-1 1 with aqueous sodium hydroxide (2 M) and extracted with EtOAc (5 x 200 mL). The combined organic phases were dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (DCM to 5% MeOH in DCM) to yield the title compound as a thick brown oil (2.42 g, 77%). m/z (ES+) 245(M+H)+. XH NMR (400 MHz, CDC13) delta 7.89-7.87 (m, 2H), 7.31 (d with fine str, J Hz, 1H), 3.89 (s, 3H), 2.38 (s, 3H), 2.31 (s, 3H), 2.11 (s, 3H).

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 72; 73
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 87

26
[ 882679-40-5 ]
methyl 4-(bromomethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); at 90℃; for 4h;	Methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.15 g, 4.16 mmol) was dissolved in ACN (27.7 mL), and N-bromosuccinimide (888 mg, 4.99 mmol) and AIBN (13.6 mg, 0.083 mmol) were added thereto, and then stirred at 90C for 4 hours. The mixture was concentrated, diluted with dichloromethane, and then filtered. The filtrate was concentrated, and then purified using silica gel chromatography to obtain the title compound (colorless oil, 1.4 g, and 95% yield). 1H NMR (300 MHz, CDCl3) delta 8.46 (d, 1H), 8.06 (dd, 1H), 7.46 (d, 1H), 4.91 (s, 2H), 3.92 (s, 3H), 1.37 (d, 12H).
	With N-Bromosuccinimide; 1,1'-azobis (cyclohexanecarbonitrile); In tetrachloromethane; at 70℃;	To a solution of SKC-0l-138 (1.50 g, 5.43 mmol) in anhydrous CCI4 (30 ml) was added N-bromosuccinimide (1.01 g, 5.70 mmol). To this stirred mixture,dicyclohexanecarbonitrile was added as a catalyst (0.07 g, 0.27 mmol) in four portions during I h. The mixture was stirred at 70C overnight. LCMS showed a major peak at 5.75 mm with the expected mass of the benzyl bromide. After cooling, the solvent was evaporated in vacuo. The crude product was dissolved in ether and filtered to remove any succinimide. The filtrate was extracted with KOH (15% w/v in H20, 3X7U ml). The aqueous phase was stirred 1-2 h at room temperature (?rt?). The solution was cooled at 0C and HC1 (6N in 1-120, ?-120 ml) was added slowly to reach pH <2. The white precipitate was collected by filtration through a fritted glass lunnel and air driedafford the 5-carboxybenzoboroxole SKC-01-150 (0.800 g, 83% yield) as a white solid powder. ?H NMR (400 MHz, DMSO-d6) 12.91 (s, IH), 9.35 (s, 1H), 8.38 (s, 1H, 8.04 ?dd,J= 8.0, 1.5 Hz, 1H), 7.52 d,J= 8.0 Hz, lH, 5.05 (s, 2H.

Reference： [1]Patent: EP2963027,2016,A1 .Location in patent: Paragraph 0473; 0474; 0475
[2]Patent: WO2014/144380,2014,A1 .Location in patent: Paragraph 0430

27
[ 882679-40-5 ]
N’-(tert-butyl)-1-hydioxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbohyrazide [ No CAS ]

Reference： [1]Patent: WO2014/144380,2014,A1

28
[ 882679-40-5 ]
N-(tert-butyl)-N’-(3,5-dimethylbenzoyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbohydrazide [ No CAS ]

Reference： [1]Patent: WO2014/144380,2014,A1
[2]Patent: WO2014/144380,2014,A1

29
[ 7697-26-9 ]
[ 882679-40-5 ]

Reference： [1]Patent: WO2014/144380,2014,A1

30
[ 882679-40-5 ]
[ 16265-11-5 ]
[ 1533440-46-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere;	Compound 7.1. Methyl 4-methyl-3-(2-methyl-lH-imidazol-5-yl)benzoate. To a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 600 mg, 2.17 mmol) in dioxane (20 mL) was added 2-methyl-4-bromo imidazole (419 mg, 2.6 mmol), Pd(dppf)Cl2 CH2Cl2 (180 mg, 0.22 mmol). The mixture was degassed argon and stirred for 10 minutes then aqueous potassium carbonate (1M, 10 mL, 10 mmol) was added and the mixture was stirred at 90 C for 18 h. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and filtered through Celite. The organic phase was washed by brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5 % MeOH in EtOAc) to yield the title compound as a foam (324 mg, 65%). m/z (ES+) 231 (M+H)+. NMR (400 MHz, CDC13) delta 8.30 (br s, 1H), 7.86 (dd, J= 7.9, 1.9 Hz, 1H), 7.32 (d, J= 7.9 Hz, 1H), 7.08 (s, 1H), 3.92 (s, 3H), 2.53 (s, 3H), 2.51 (s, 3H)

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 92

31
[ 882679-40-5 ]
3-(5-iodo-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)oxetan-3-ol [ No CAS ]
methyl 3-(2-(3-hydroxyoxetan-3-yl)-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; for 7h;Inert atmosphere;	Compound 192.4. Methyl 3-(2-(3-hydroxyoxetan-3-yl)-4-methyl-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazol-5-yl)-4-methylbenzoate. Into a 100-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 4-methyl-3-(tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate (compound 5.4, 282.7 mg, 1.02 mmol) in dioxane (12 mL). A solution of K3PO4 (904.9 mg, 4.26 mmol) in water (1.2 mL), 3-(5-iodo-4-methyl-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazol-2-yl)oxetan-3-ol (compound 192.3, 350 mg, 0.85 mmol) and Pd(dppf)2Cl2 (62.4 mg, 0.09 mmol) were added to the reaction. The mixture was stirred for 7h. The reaction mixture was cooled, then diluted with 60 mL of EtOAc. The solids were removed by filtration, the filtrate was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (2:3) eluent to furnish 220 mg (60%) of the title compound as an orange oil.

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 235

32
[ 882679-40-5 ]
3-(5-iodo-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)oxetan-3-ol [ No CAS ]
methyl 3-(2-(3-hydroxyoxetan-3-yl)-4-methyl-1H-imidazol-5-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

33
[ 882679-40-5 ]
5-iodo-1H-imidazole-2-carbonitrile [ No CAS ]
methyl 3-(2-cyano-1H-imidazol-5-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); XPhos; In 1,2-dimethoxyethane; water; at 90℃;Inert atmosphere;	Compound 234.3. Methyl 3-(2-cyano-lH-imidazol-5-yl)-4-methylbenzoate. Into a 100-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-iodo-lH-imidazole-2-carbonitrile (compound 234.2, 700 mg, 3.20 mmol) in a solvent mixture of DME and Iota0 (30/3 mL). Methyl 4-methyl-3-(tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 1.06 g, 3.84 mmol), K3PO4 (2.71 g, 12.8 mmol), Xphos (152 mg, 0.32 mmol), Pd(PPh3)4 (369 mg, 0.32 mmol) were added to the reaction. The reaction mixture was stirred overnight at 90 C, then concentrated under reduced pressure. The residue was diluted with 50 mL of ethyl acetate, then was washed with 3 x 20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1/2) as eluent to furnish 160 mg (21%) of the title compound as a white solid.

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 272; 273

34
[ 882679-40-5 ]
5-iodo-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazole [ No CAS ]
methyl 4-methyl-3-(2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	Compound 241.2. Methyl 4-methyl-3-(2-(tetrahydro-2H-pyran-4-yl)-lH- imidazol-5-yl)benzoate. _:Into a 50-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-iodo-2- (tetrahydro-2H-pyran-4-yl)-lH-imidazole (compound 241.1, 400 mg, 1.44 mmol) in dioxane (15 mL). Methyl 4-methyl-3-(tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 397 mg, 1.44 mmol), potassium carbonate (993 mg, 7.18 mmol), water(1.5 mL) and Pd(dppf)C12 (105 mg, 0.14 mmol, 0.10 equiv) were added to the reaction. The reaction mixture was stirred overnight at 90 C, then diluted with 120 mL of EtOAc. The organic layer was washed with 3 x 40 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate as eluent to furnish 260 mg (60%) of the title compound as red oil.

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 281

35
[ 882679-40-5 ]
3-iodo-4-methoxy-1H-pyrazole [ No CAS ]
methyl 3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	Compound 244.6. Methyl 3-(4-methoxy-lH-pyrazol-5-yl)-4-methylbenzoate. Into a 50-mL three neck round-bottom flask, purged and maintained with nitrogen, was placed a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (414 mg, 1.50 mmol) in dioxane (6 mL). Potassium carbonate (2 M, 2.5 mL, 5.00 mmol), 3-iodo- 4-methoxy-lH-pyrazole (compound 244.5, 224 mg, 1.00 mmol), Pd(dppf)Ci2 (73 mg, 0.10 mmol) were added to the reaction and the resulting mixture was stirred overnight at 90 C. The resulting mixture was cooled, then diluted with EtOAc (80 mL) and washed with brine (2 x 30 mL), dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1/1) as eluent to obtain the title compound as a yellow oil (180 mg, 73%).

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 286; 287

36
[ 882679-40-5 ]
methyl 3-(5-chloro-2-methyl-1H-imidazol-4-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

37
[ 882679-40-5 ]
3-(5-chloro-2-methyl-1H-imidazol-4-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

38
[ 882679-40-5 ]
4-methyl-3-(2-methyl-1H-imidazol-4-yl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

39
[ 882679-40-5 ]
methyl 3-(4-chloro-2-cyano-1H-imidazol-5-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

40
[ 882679-40-5 ]
3-(4-chloro-2-cyano-1H-imidazol-5-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

41
[ 882679-40-5 ]
4-chloro-5-(5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-methylphenyl)-1H-imidazole-2-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

42
[ 882679-40-5 ]
methyl 3-(4-chloro-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

43
[ 882679-40-5 ]
3-(4-chloro-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

44
[ 882679-40-5 ]
4-(1-(3-(4-chloro-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)-4-methylbenzoyl)azetidin-3-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

45
[ 882679-40-5 ]
3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

46
[ 882679-40-5 ]
4-(1-(3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoyl)azetidin-3-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

47
[ 882679-40-5 ]
methyl 3-(4-cyano-1H-pyrazol-5-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2015/95767,2015,A1

48
[ 882679-40-5 ]
3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-4-carbonitrile [ No CAS ]
methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	Compound 256.3. Methyl 3-(4-cyano-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- pyrazol-5-yl)-4-methylbenzoate. Into a 250-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-iodo- l-((2-(trimethylsilyl)ethoxy)methyl)-lH-pyrazole-4-carbonitrile (compound 256.2, 2.73 g, 7.82 mmol, 1.00 equiv) in dioxane (30 mL). Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzoate (2.59 g, 9.38 mmol), Pd(dppf)Ci2 (570 mg, 0.78 mmol), and a solution of potassium carbonate (3.24 g, 23.4 mmol) in water (3 mL) were added to the reaction. The resulting mixture was stirred overnight at 90 C, then cooled and diluted with EtOAc (500 mL). The resulting mixture was washed with brine (2 x 100 mL), dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (40: 1) as eluent to obtained the title compound as a yellow oil (1.9 g, 65%).

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 299; 300

49
[ 882679-40-5 ]
methyl 4-(((2-bromo-5-(methoxymethoxy)benzyl)oxy)methyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]

Reference： [1]Patent: EP2963027,2016,A1

50
[ 882679-40-5 ]
methyl 9-(methoxymethoxy)-5,7-dihydrodibenzo[c,e]oxepin-2-carboxylate [ No CAS ]

Reference： [1]Patent: EP2963027,2016,A1

51
[ 882679-40-5 ]
methyl 9-hydroxy-5,7-dihydrodibenzo[c,e]oxepin-2-carboxylate [ No CAS ]

Reference： [1]Patent: EP2963027,2016,A1

52
[ 882679-40-5 ]
methyl 9-(2-ethoxyethoxy)-5,7-dihydrodibenzo[c,e]oxepin-2-carboxylate [ No CAS ]

Reference： [1]Patent: EP2963027,2016,A1

53
[ 882679-40-5 ]
3-(5-(3-hydroxyoxetan-3-yl)-6-methoxypyridin-3-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2016/38582,2016,A1

54
[ 882679-40-5 ]
3-(5-(3-hydroxyoxetan-3-yl)-6-methoxypyridin-3-yl)-4-methyl-N-(2-(trifluoromethyl)pyridin-4-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/38582,2016,A1

55
[ 882679-40-5 ]
N-(3-(difluoromethyl)phenyl)-3-(5-(3-hydroxyoxetan-3-yl)-6-methoxypyridin-3-yl)-4-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2016/38582,2016,A1

56
[ 882679-40-5 ]
3-(5-bromo-2-methoxypyridin-3-yl)oxetan-3-ol [ No CAS ]
methyl 3-(5-(3-hydroxyoxetan-3-yl)-6-methoxypyridin-3-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Microwave irradiation;	j00269J Step 1: To a mixture of (1.0 equiv). methyl 4-methyI.-3(4,4,5,54etramethyI.- L3,2dioxahorolan2.-yl)benzoate (1.3 equiv.) and PdC12(dppO.DCM adduct (008 equiv.) in DME (0.19 M) was added Na2CO3 (2M aqueous solution. 3.0 equiv.). The mixture was stirred at 120 C in microwave for 15 mm. The reaction was partitioned between brine and ethyl acetate, the organic layer was dried over sodium sulfate and concentrated to give methyl 3-(53hydroxyoxetaru3-yi)6.- methoxypyridin.-3yi)4.-methylbenzoate in quantitative yield. The crude material was used for the next step without further purification. LCMS (m/r) (M+H) = 3300. Rt = 0.76 mm.

Reference： [1]Patent: WO2016/38582,2016,A1 .Location in patent: Paragraph 00269

57
[ 882679-40-5 ]
[ 1269492-47-8 ]
tert-butyl 4-(3-cyano-5-(5-(methoxycarbonyl)-2-methylphenyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; 1,2-dichloro-ethane; at 120℃; for 0.25h;Microwave irradiation;	To a mixture of tert-butyl 4-(5-bromo-3-cyanopyridin-2-yl)piperazine- 1-carboxylate (1.0 equiv.), methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzoate (1.1 equiv.) and PdCl2(dppf).CH2Cl2 adduct (0.08 equiv.) in DME (0.36 M) was added Na2CO3 (3.0 equiv, 2M aqueous solution). The mixture was stirred at 120 C in the microwave for 15 min. LC-MS showed complete conversion. Added brine and EtOAc, the organic layer was dried over sodium sulfate and concentrated and purified by ISCO (0-100% EtOAc/Heptane) to give tert-butyl 4-(3-cyano-5-(5-(methoxycarbonyl)-2- methylphenyl)pyridin-2-yl)piperazine-1-carboxylate in 74% yield. LCMS (m/z) (M+H) = 381.2, Rt = 1.13 min.

Reference： [1]Patent: WO2016/38583,2016,A1 .Location in patent: Paragraph 00155

58
[ 882679-40-5 ]
3-(5-cyano-6-(piperazin-1-yl)pyridin-3-yl)-4-methyl-N-(2-(trifluoromethyl)pyridin-4-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/38583,2016,A1

59
[ 882679-40-5 ]
3-(5-cyano-6-(piperazin-1-yl)pyridin-3-yl)-4-methyl-N-(2-(methylsulfonyl)pyridin-4-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/38583,2016,A1

60
[ 882679-40-5 ]
C₂₉H₂₉F₃N₆O₃ [ No CAS ]

Reference： [1]Patent: WO2016/38583,2016,A1

61
[ 882679-40-5 ]
C₂₉H₃₂N₆O₅S [ No CAS ]

Reference： [1]Patent: WO2016/38583,2016,A1

62
[ 882679-40-5 ]
3-(6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-cyanopyridin-3-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2016/38583,2016,A1

63
[ 882679-40-5 ]
6-bromo-2-(methylthio)quinazoline [ No CAS ]
methyl 4-methyl-3-(2-(methylthio)quinazolin-6-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.04 g	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; water; at 70℃; for 24h;Inert atmosphere;	A suspension of the product from step (i) above (12.93 g, 50.7 mmol), methyl 4-methyl-3- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate (14.0 g, 50.7 mmol) and cesium carbonate (49.75 g, 153 mmol) in THF/dioxane/water (200 mL; 2:2:1) was degassed with N2 (under sonication) and then treated with PdCI2(PPh3)2 (3.56 g, 5.07 mmol). The suspension was further degassed and then stirred at 7000 for 24 h. The reaction mixture was then held at rt for 48 h. The reaction mixture was partitioned between EtOAc (1 L) and 20% brine (1 L) and the organics washed with brine (2 x 1 L), dried (MgSO4) and evaporated to afford a brown oil. The crude product was purified by chromatography on silica gel (330 g column, 0-20% EtOAc/iso-hexanes). The resulting yellow solid was triturated from 30% diethyl ether/isohexanes to afford the sub-title compound (9.04 g) as an off-white solid. The liquours were evaporated to afford a second crop of the sub-title compound (3.02 g) as a yellow solid.1H NMR (400 MHz, DMSO-d6) O 9.46 (d, 1H), 8.12 (dd, 1H), 8.01 (dd, 1H), 7.97 - 7.86 (m, 3H), 7.58-7.50 (m, 1H), 3.87 (5, 3H), 2.66 (5, 3H), 2.36 (5, 3H).

Reference： [1]Patent: WO2016/51186,2016,A1 .Location in patent: Page/Page column 55

64
[ 882672-05-1 ]
[ 882679-40-5 ]
methyl 3-(2-chloroquinazolin-6-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
510 mg	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; at 90℃; for 1.0h;Inert atmosphere;	(i) Methyl 3-(2-chloroguinazolin-6-yl)-4-methylbenzoateA mixture of 6-bromo-2-chloroquinazoline (780 mg, 3.20 mmol) and methyl 4-methyl-3- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate (1000 mg, 3.62 mmol) in 1,2- dimethoxyethane (3 mL) and 1 M NaHCO3 solution (10 mL, 10.00 mmol) was purged with nitrogen for 5 minutes. The mixture was heated to 90C before adding Pd(Ph3P)4 (200 mg, 0.173 mmol) and stirring for 1 h. The mixture was diluted with water (150 mL) and extracted with diethyl ether (3 x 150 mL). The combined organic phases were washed with water (150 mL), 20 % brine (150 mL) and saturated brine (150 mL). The organic phase was dried (MgSO4) and concentrated to give a yellow oil which was purified by chromatography on the Companion (80 g column, 0-30% EtOAc/isohexane) to afford the sub-title compound (510 mg) as a cream solid.LCMS mlz 313 (M+H) (ES)

Reference： [1]Patent: WO2016/51186,2016,A1 .Location in patent: Page/Page column 45

65
[ 882679-40-5 ]
methyl 3-(2-((3-methoxy-5-((2-morpholinoethyl)carbamoyl)phenyl)amino)quinazolin-6-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

66
[ 882679-40-5 ]
3-(2-((3-methoxy-5-((2-morpholinoethyl)carbamoyl)phenyl)amino)quinazolin-6-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

67
[ 882679-40-5 ]
N-(5-(tert-butyl)-3-carbamoyl-2-methoxyphenyl)-3-(2-((3-methoxy-5-((2-morpholinoethyl)carbamoyl)phenyl)amino)quinazolin-6-yl)-4-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

68
[ 882679-40-5 ]
N-(5-(tert-butyl)-3-(dimethylphosphoryl)-2-methoxyphenyl)-3-(2-((3-methoxy-5-((2-morpholinoethyl)carbamoyl)phenyl)amino)quinazolin-6-yl)-4-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

69
[ 882679-40-5 ]
N-(5-(tert-butyl)-2-methoxy-3-(methylsulfonamido)phenyl)-3-(2-((3-methoxy-5-((2-morpholinoethyl)carbamoyl)phenyl)amino)quinazolin-6-yl)-4-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

70
[ 882679-40-5 ]
methyl 3-(2-((3-methoxy-5-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)amino)-quinazolin-6-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

71
[ 882679-40-5 ]
3-(2-((3-methoxy-5-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)amino)quinazolin-6-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

72
[ 882679-40-5 ]
3-(2-((3-methoxy-5-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)amino)quinazolin-6-yl)-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

73
[ 882679-40-5 ]
N-(5-(tert-butyl)-2-methoxy-3-(methylsulfonamido)phenyl)-3-(2-((3-methoxy-5-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)amino)quinazolin-6-yl)-4-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2016/51186,2016,A1

74
[ 882679-40-5 ]
4-bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine [ No CAS ]
(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-[5'-(methoxycarbonyl)-2'-methylbiphenyl-4-yl]propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h;Inert atmosphere;	Example 67A (2S)-2-[(trans-4-[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-[5'-(methoxycarbonyl)-2'-methylbiphenyl-4-yl]propanoic acid 4-Bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine (43.4 g, 90 mmol) and <strong>[882679-40-5]methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate</strong> (33.6 g, 117 mmol) were dissolved in DMF (400 ml), and an aqueous 2N sodium carbonate solution (135 ml) was added. The reaction solution was degassed with argon for 5 min, after which the catalyst 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride (6.6 g, 9.0 mmol) was added. The mixture was stirred at 120 C. (oil bath temperature) for 30 min. The contents of the flask were filtered through kieselguhr and washed through with ethyl acetate. The solvent was removed on a rotary evaporator and the residue was partitioned between ethyl acetate and 10% strength aqueous citric acid solution. The mixture was extracted with ethyl acetate, the combined organic phases were washed with saturated aqueous sodium chloride solution and dried over magnesium sulphate, and the solvent was removed on a rotary evaporator. The residue was suspended in diethyl ether and the solid was filtered off with suction, washed with diethyl ether and dried under high vacuum. This gave 38.1 g (77% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=ppm 0.71-0.89 (m, 2H), 1.03-1.29 (m, 3H), 1.36 (s, 9H), 1.45-1.54 (m, 1H), 1.57-1.73 (m, 3H), 1.98-2.10 (m, 1H), 2.27 (s, 3H), 2.74 (m, 2H), 2.85-2.95 (m, 1H), 3.14 (dd, 1H), 3.84 (s, 3H), 4.50 (br. s., 1H), 6.71-6.82 (m, 1H), 7.23-7.35 (m, 4H), 7.45 (d, 1H), 7.71 (d, 1H), 7.85 (dd, 1H), 8.03 (d, 1H), 12.68 (br. s, 1H). LC-MS (Method 1): Rt=1.13 min; MS (ESIpos): m/z=553 [M+H]+.

Reference： [1]Patent: US2016/237067,2016,A1 .Location in patent: Paragraph 0670; 0671; 0672; 0673

75
[ 882679-40-5 ]
4-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]
methyl 4'-[(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-oxo-3-[4-(2H-tetrazol-5-yl)phenyl]amino}propyl]-6-methylbiphenyl-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; for 4h;Reflux;	Example 11A Methyl 4'-[(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-oxo-3-[4-(2H-tetrazol-5-yl)phenyl]amino}propyl]-6-methylbiphenyl-3-carboxylate 1000 mg (1.60 mmol) of 4-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide, 184 mg (0.16 mmol) of tetrakis(triphenylphosphine)palladium(0) and 881 mg (3.19 mmol) of <strong>[882679-40-5]methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate</strong> were taken up in 12 ml of 1,2-dimethoxyethane and 5 ml of ethanol. After addition of 3 ml of 2N aqueous sodium carbonate solution, the reaction mixture was stirred at reflux for 4 h and at RT for 16 h, the salts were then filtered off over kieselguhr and the filtrate was separated by column chromatography on silica gel (mobile phase: ethyl acetate?ethyl acetate/methanol 8:2). This gave 1024 mg (88% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=0.73-0.92 (m, 2H), 1.09-1.31 (m, 3H), 1.36 (s, 9H), 1.48-1.57 (m, 1H), 1.59-1.73 (m, 3H), 2.06-2.16 (m, 1H), 2.24 (s, 3H), 2.69-2.79 (m, 2H), 2.89-3.00 (m, 1H), 3.08-3.18 (m, 1H), 3.83 (s, 3H), 4.70-4.81 (m, 1H), 6.74-6.82 (m, 1H), 7.28 (d, 2H), 7.35-7.48 (m, 3H), 7.68-7.73 (m, 1H), 7.74-7.81 (m, 2H), 7.81-7.86 (m, 1H), 7.93-8.02 (m, 2H), 8.18 (d, 1H), 10.39 (s, 1H), 16.7 (br. s, 1H). LC-MS (Method 1): Rt=1.14 min; MS (ESIneg): m/z=694 [M-H]-.

Reference： [1]Patent: US2016/237067,2016,A1 .Location in patent: Paragraph 0484; 0485; 0486; 0487

76
[ 882679-40-5 ]
tert-butyl 4-({4'-[(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)-carbonyl]amino}-3-oxo-3-[4-(2H-tetrazol-5-yl)phenyl]amino}propyl]-6-methylbiphenyl-3-yl}carbonyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

77
[ 882679-40-5 ]
tert-butyl [(trans-4-[(2S)-3-{5'-[(trans-4-hydroxycyclohexyl)carbamoyl]-2'-methylbiphenyl-4-yl}-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

78
[ 882679-40-5 ]
tert-butyl [(trans-4-[(2S)-3-[2'-methyl-5'-(morpholin-4-ylcarbonyl)biphenyl-4-yl]-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

79
[ 882679-40-5 ]
tert-butyl [(trans-4-[(2S)-3-{2'-methyl-5'-[(2-oxopiperidin-4-yl)carbamoyl]biphenyl-4-yl}-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

80
[ 882679-40-5 ]
tert-butyl [(trans-4-[(2S)-3-[4'-methyl-3'-(morpholin-4-ylcarbonyl)biphenyl-4-yl]-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

81
[ 882679-40-5 ]
trans-4-(aminomethyl)-N-[(2S)-3-[2'-methyl-5'-(piperazin-1-ylcarbonyl)biphenyl-4-yl]-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]cyclohexanecarboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

82
[ 882679-40-5 ]
4'-[(2S)-2-([trans-4-(aminomethyl)cyclohexyl]carbonyl}amino)-3-oxo-3-[4-(2H-tetrazol-5-yl)phenyl]amino}propyl]-N-(trans-4-hydroxycyclohexyl)-6-methylbiphenyl-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

83
[ 882679-40-5 ]
trans-4-(aminomethyl)-N-[(2S)-3-[2'-methyl-5'-(morpholin-4-ylcarbonyl)biphenyl-4-yl]-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]cyclohexanecarboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

84
[ 882679-40-5 ]
4'-[(2S)-2-([trans-4-(aminomethyl)cyclohexyl]carbonyl}amino)-3-oxo-3-[4-(2H-tetrazol-5-yl)phenyl]amino}propyl]-6-methyl-N-(2-oxopiperidin-4-yl)biphenyl-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

85
[ 882679-40-5 ]
trans-4-(aminomethyl)-N-[(2S)-3-[4'-methyl-3'-(morpholin-4-ylcarbonyl)biphenyl-4-yl]-1-oxo-1-[4-(2H-tetrazol-5-yl)phenyl]amino}propan-2-yl]cyclohexanecarboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

86
[ 882679-40-5 ]
4'-[(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-oxo-3-[4-(2H-tetrazol-5-yl)phenyl]amino}propyl]-6-methylbiphenyl-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2016/237067,2016,A1

87
[ 45644-21-1 ]
[ 882679-40-5 ]
methyl 3-(6-aminopyridin-2-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃;	Example 129A methyl 3-(6-aminopyridin-2-yl)-4-methylbenzoate 6-chloropyridin-2-amine (0.129 g, 1 mmol), <strong>[882679-40-5]methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate</strong> (0.304 g, 1.100 mmol), potassium carbonate (0.332 g, 2.400 mmol), and PdCl2dppf (0.037 g, 0.050 mmol) in dimethoxyethane (3.4 mL) and water (1.7 mL) were heated at 80 C. overnight. The mixture was diluted with ethyl acetate (20 mL) and washed with water (3*5 mL) and brine (5 mL) sequentially. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The dark brown crude oil was purified by silica gel chromatography, eluting with 10 to 70% ethyl acetate-heptanes, to afford the title compound as a white solid (0.085 g, 35%). 1H NMR (500 MHz, DMSO-d6) delta 7.94-7.79 (m, 2H), 7.51-7.37 (m, 2H), 6.61 (dd, J=7.3, 0.9 Hz, 1H), 6.44 (dd, J=8.3, 0.9 Hz, 1H), 6.01 (s, 2H), 3.84 (s, 3H), 2.39 (s, 3H). MS (DCI+) m/z 243.0 (M+H).

Reference： [1]Patent: US2017/15675,2017,A1 .Location in patent: Paragraph 1235

88
[ 882679-40-5 ]
3-(6-[(7R)-2,2-difluoro-7-methyl-6,7-dihydro-2H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino}pyridin-2-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: US2017/15675,2017,A1

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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 882679-40-5 ] {[proInfo.proName]}

Quality Control of [ 882679-40-5 ]

Related Doc. of [ 882679-40-5 ]

Product Details of [ 882679-40-5 ]

Calculated chemistry of [ 882679-40-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 882679-40-5 ]

Application In Synthesis of [ 882679-40-5 ]

[ 882679-40-5 ] Synthesis Path-Upstream 1~8

[ 882679-40-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 882679-40-5 ]

Organoboron

Aryls

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 882679-40-5 ]