[ CAS No. 913836-14-3 ] {[proInfo.proName]}

Name: 913836-14-3|(3-Chloro-5-methylphenyl)boronic acid|97%
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SKU: A298802
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Quality Control of [ 913836-14-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 913836-14-3 ]

Product Details of [ 913836-14-3 ]

CAS No. :	913836-14-3	MDL No. :	MFCD09027241
Formula :	C₇H₈BClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QXHLBINWDJITMJ-UHFFFAOYSA-N
M.W :	170.40	Pubchem ID :	21183168
Synonyms :

Calculated chemistry of [ 913836-14-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.24
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) :	-6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	0.33
Log Po/w (MLOGP) :	1.21
Log Po/w (SILICOS-IT) :	0.34
Consensus Log Po/w :	0.74

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.38
Solubility :	0.709 mg/ml ; 0.00416 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	0.875 mg/ml ; 0.00513 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.29
Solubility :	0.882 mg/ml ; 0.00518 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 913836-14-3 ]

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 [ 913836-14-3 ]

* 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 [ 913836-14-3 ]
Downstream synthetic route of [ 913836-14-3 ]

[ 913836-14-3 ] Synthesis Path-Upstream 1~2

1
[ 108-41-8 ]
[ 913836-14-3 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 5, p. 757 - 760

2
[ 502630-89-9 ]
[ 913836-14-3 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 5, p. 757 - 760

[ 913836-14-3 ] Synthesis Path-Downstream 1~21

1
[ 913836-14-3 ]
[ 216485-72-2 ]
(3'-chloro-6-methanesulfonyl-2,5'-dimethyl-biphenyl-3-yl)-(1-ethyl-5-hydroxy-1<i>H</i>-pyrazol-4-yl)-methanone [ No CAS ]

Reference： [1]Pest Management Science,2002,vol. 58,p. 1175 - 1186

2
[ 98-54-4 ]
[ 913836-14-3 ]
(3-chloro-5-methylphenyl)-4-tert-butylphenyl ether [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 761 - 764

3
[ 502630-89-9 ]
[ 913836-14-3 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 757 - 760

4
[ 108-41-8 ]
[ 913836-14-3 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 757 - 760

5
[ 78686-83-6 ]
[ 913836-14-3 ]
[ 761446-44-0 ]
[ 1112849-95-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 2 5-(3-Chloro-5-methvIphenyl)-2-(l -methyl- 1H-pyrazol-4-vQ nicotinic acid (2-2)To a solution of methyl 2-chloro-5-iodonicotonate {2?_, 1.00 g, 3.36 mmol) in dimethylformamide (15 mL) at 25 C was added 3-chloro-5-methylboronic acid (0.573 g, 3.36 mmol; synthesized via procedures found in Org. Lett. 2007, P, 757-760), PdCl2dppf (0.246 g, 0.336 mmol) followed by IM aqueous cesium carbonate (13.5 mL, 13.5 mmol) and the system was stirred for 4h at 25 C. The system was partitioned between water and EtOAc, and dried over magnesium sulfate. Filtration and concentration yielded a brown solid which upon tritiration with ether afforded a tan solid. To this tan solid (0.05 g, 0.169 mmol) in dimethylformamide (0.8 mL) at 25 C was added l-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H pyrazole (0.038 g, 0.186 mmol), PdCl2dppf (0.012 g, 0.017 mmol) followed by 4M aqueous cesium carbonate (0.67 mL, 0.675 mmol) and the system was stirred for 15 minutes at 135 C in the microwave. The system was partitioned between water and EtOAc. The aqueous layer was then acidified using 25% citric acid to a pH of 3, extracted with EtOAc and the organic layer was dried over magnesium sulfate. Filtration and concentration afforded the title compound (2-2) as a cream solid. ESI+ MS [M+H]+ C17H14ClN3O2 = 328.0.

Reference： [1]Patent: WO2009/20642,2009,A1 .Location in patent: Page/Page column 47-48

6
[ 78686-83-6 ]
[ 913836-14-3 ]
C₁₄H₁₁Cl₂NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; N,N-dimethyl-formamide; at 25℃; for 4h;	5- -chloro-5-methylphenyl)-2-morpholin-4-ylnicotinic acid (4-2)To a solution of methyl 2-chloro-5-iodonicotonate (4-1, 9.34 g, 31.5 mmol) in dimethylformamide (157 mL) at 25 C was added 3-chloro-5-methylboronic acid (5.35 g, 31.4 mmol), PdCl2dppf (2.3 g, 3.14 mmol) followed by cesium carbonate (41.0 g, 126 mmol) and water (10.0 mL, 565 mmol) and the system was stirred for 4 h at 25 C. The system was partitioned between water and EtOAc, and dried over magnesium sulfate. Filtration and concentration yielded a brown solid which upon purification via normal phase chromatography (0-15% EtOAc in Hx) afforded a white solid. To this white solid (4.0 g, 13.5 mmol) in dioxane (67.5 mL) at 25 C was added morpholine (5.88 g, 67.5 mmol) and the system was heated to 90 C for 3h. The solvent was removed in vacuo and the resulting residue was partitioned between water and EtOAc followed by purification via normal phase chromatography (5 -15% EtOAc in Hx) to yield a white foam. To this white foam (4.2 g, 12.11 mmol) in THF (30 mL) and MeOH (30 mL) was added KOH (5.19 mL, 36.3 mmol) and stirred at ambient temperature overnight. The system was then acidified using 6 N HCl to a pH of 2.0 and the solvents were azeotroped off with toluene to afford the title compound (4) as a yellow powder. HRMS [M+H] Ci7Hi2ClN2O3 calc'd 333.1002, found 333.1000.

Reference： [1]Patent: WO2009/20642,2009,A1 .Location in patent: Page/Page column 57-58

7
[ 1186403-14-4 ]
[ 913836-14-3 ]
[ 1137639-44-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4059 - 4063

8
[ 1225016-33-0 ]
[ 913836-14-3 ]
[ 1225016-11-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 100℃; for 18h;	6-(3-chloro-5-methylphenyl)-N-(3.4-dimethoxybenzyl)-3-morpholin-4-ylpyridazine-4- carboxamide (2-2)A suspension of 6-chloro-N-(3,4-dimethoxybenzyl)-3-morpholin-4-ylpyridazine- 4-carboxamide QzI, 0.034 g, 0.087 mmol, 1.0 equiv), <strong>[913836-14-3]3-chloro-5-methylboronic acid</strong> (0.026 g, 0.151 mmol, 1.75 equiv; synthesized via procedures found in Org. Lett. 2007, 9, 757-760), PdCl2(dppf) (0.013 g, 0.017 mmol, 0.2 equiv) and Cs2CO3 (0.085 g, 0.260 mmol, 3.0 equiv) in dioxane (0.6 mL) was made and heated to 1000C for 18 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic phase was washed with water (3 times). The combined organic phase was dried over magnesium sulfate and concentrated. The reaction mixture was filtered and purified via normal phase chromatography (5 to 85% EtOAc in hexanes) to afford the product Q1T) as an off-white solid. HRMS [M+H] C25H27ClN4O4 calc'd 483.1794, found 483.1805.

Reference： [1]Patent: WO2010/51238,2010,A1 .Location in patent: Page/Page column 43-44

9
[ 1565836-98-7 ]
[ 913836-14-3 ]
[ 1565837-11-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		Compound3n (1 g, 2.95 mmol) was reacted asdescribed in Section 2.1 to give 4nas blue solid (0.417 g, 87%); Rf (20% EtOAc-Hexane) 0.68, blue spot; mp 106-108C;1H NMR (400 MHz, DMSO) delta: 2.153 (s, 3H, -CH3), 2.401(s, 3H, -CH3), 2.518 (s, 3H, -CH3), 6.696-6.719 (d, J=9.2Hz, 1H, Ar-H), 7.049-7.092 (t, J=9.6 Hz & J=7.6 Hz, 2H, Ar-H), 7.141-7.191(m, 2H, Ar-H), 7.251-7.324 (s, 2H, Ar-H), 7.362-7.417 (m, 3H, Ar-H),8.168-8.188 (d, J=8 Hz, 2H, Ar-H); 13CNMR (100 MHz, DMSO) delta: 20.80,22.27, 31.67, 114.54, 119.03, 120.17, 121.32, 123.82, 124.86, 129.82, 129.85,130.39, 131.16, 133.48, 140.24, 157.38, 158.13, 160.58, 161.03, 203.57 ; IR(KBr, cm-1): 2961, 2351, 1691, 1643, 1527, 1238, 707, 835.Anal.Calcdfor C22H22ClN3O2: C, 72.81; H,4.94; N, 6.33. Found: C, 72.90; H, 4.96; N, 6.49.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1456 - 1460

10
[ 931-59-9 ]
[ 913836-14-3 ]
[ 1393715-53-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With Pd(2-[2-(benzylthio)phenyliminomethyl]-4-bromophenol-(H))Cl; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 5h;Sealed tube; Inert atmosphere;	General procedure: A sealed tube was charged with sulfenyl chloride 2a (219mg, 1 mmol), phenylboronic acid (3a) (135 mg, 1 mmol),K2CO3 (254 mg, 2 mmol), catalyst 1a (2 mol%, 10 mg) andDMF (2 mL). The mixture was stirred at 90 C under an N2atm for 5 h. After completion of the reaction, the mixturewas cooled to r.t. and extracted with EtOAc (2 × 10 mL). The combined extracts were dried over anhydrous Na2SO4,filtered and the solvent removed under reduced pressure.The crude residue was purified by flash chromatographyover silica gel to provide product 4a (166 mg, 89%).

Reference： [1]Synlett,2014,vol. 25,p. 866 - 870

11
3-amino-6-bromo-N-cyclopentylpyrazine-2-carboxamide [ No CAS ]
[ 913836-14-3 ]
3-amino-6-(3-chloro-5-methylphenyl)-N-cyclopentylpyrazine-2-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 6753 - 6765

12
3-amino-6-bromo-N-(pentan-3-yl)pyrazine-2-carboxamide [ No CAS ]
[ 913836-14-3 ]
3-amino-6-(3-chloro-5-methylphenyl)-N-(pentan-3-yl)pyrazine-2-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 6753 - 6765

13
(2S)-([6-bromo-3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-5-ylmethyl]methyl-amino}methyl)pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 913836-14-3 ]
(2S)-2-([6-(3-chloro-5-methyl-phenyl)-3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-5-ylmethyl]methyl-amino}methyl)pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
500 mg	With tetrakis(triphenylphosphine) palladium(0); potassium triphosphate; In 1,4-dioxane; water; at 50℃; for 5h;Inert atmosphere; Sealed tube;	Step 5, preparation of (2S)-2-([6-(3-chloro-5-methyl-phenyl)-3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-5-ylmethyl]-methyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester: (S)-([6-bromo-3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-5-ylmethyl]-methyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.2 g, 2.1 mmol), tetra-kis(triphenylphosphine)-palladium (122 mg, 0.11 mmol), potassium triphosphate (1.5 g, 6 mmol), and <strong>[913836-14-3]3-chloro-5-methylphenylboronic acid</strong> (535 mg, 3.0 mmol) were mixed into a mixture of dioxane (30 ml) and water (3 ml), then the reaction mixture was bubbled with N2 for 10 min, then sealed and heated to 50 C. for 5 hrs. After cooled to rt, the crude was loaded on silica gel directly and purified using DCM and MeOH as eluents to offer the desired product (500 mg). (M+H)+: 618.2.

Reference： [1]Patent: US2017/2001,2017,A1 .Location in patent: Paragraph 0355

14
methyl 4-bromo-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate [ No CAS ]
[ 913836-14-3 ]
4-(3-chloro-5-methylphenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		Nitrogen was passed through a solution of dioxane/H2O (4/1) and this solution ( 2.0 mL) was then added to a mixture of the methyl 4-bromo-1-(4-(3,4-dichlorophenyl)-5- (isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate (50 mg, 0.096 mmol), (3- chloro-5-methylphenyl)boronic acid (20 mg, 0.12 mmol) and Na2CO3 (51 mg, 0.48 mmol) followed by the addition of the catalyst Pd(PPh3)4 (11 mg, 0.010 mmol). The reaction mixture was heated at 85 oC for 16 hours. Add LiOH (12 mg, 0.48 mmol) and the reaction mixture was stirred in the microwave at 110 oC for 10 min. Add more LiOH (12 mg, 0.48 mmol) and stirring in the microwave at 110 oC was continued for 10 min. Evaporated in vacuo. The crude product was purified by semi-prep HPLC-MS (column X-Bridge 30x50, eluted with 70- 90% MeCN/NH4CO2H 10 mM, pH 3.8/Flow 45 ml/min/10 min) and afforded the title compound (22 mg, 0.040 mmol, 42%) as a yellow solid after lyophilization. 1H NMR (500 MHz, DMSO) delta 8.20 (d, J = 2.1 Hz, 1H), 8.02 (dd, J = 8.5, 2.1 Hz, 1H), 7.76 (d, J = 8.5 Hz, 1H), 7.32 (s, 1H), 7.30 (s, 1H), 7.25 (s, 1H), 3.41- 3.31 (m, 1H), 2.36 (s, 3H), 2.30 (s, 3H), 1.24 (d, J = 6.7 Hz, 6H). MS (m/z): 552.0 [M+1]+.
42%		Nitrogen was passed through a solution of dioxane/H20 (4/1) and this solution ( 2.0 mL) was then added to a mixture of the methyl 4-bromo-1-(4-(3,4-dichlorophenyl)-5- (isopropylthio)thiazol-2-yl)-3-methyl- 1 H-pyrazole-5-carboxylate (50 mg, 0.096 mmol), (3- chloro-5-methylphenyl)boronic acid (20 mg, 0.12 mmol) and Na2003 (51 mg, 0.48 mmol) followed by the addition of the catalyst Pd(PPh3)4 (11 mg, 0.010 mmol). The reaction mixture was heated at 85 00 for 16 hours. Add LiOH (12 mg, 0.48 mmol) and the reaction mixture was stirred in the microwave at 11000 for 10 mm. Add more LiOH (12 mg, 0.48 mmol) and stirring in the microwave at 110 00 was continued for 10 mm. Evaporated in vacuo. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30x50, eluted with 70- 90% MeCN/NH4002H 10 mM, pH 3.8/Flow 45 mI/min/lO mm) and afforded the title compound (22 mg, 0.040 mmol, 42%) as a yellow solid after lyophilization. 1H NMR (500 MHz, DMSO) O 8.20 (d, J= 2.1 Hz, 1H), 8.02 (dd, J= 8.5, 2.1 Hz, 1H), 7.76 (d, J= 8.5 Hz, 1H), 7.32 (s, 1H), 7.30 (s, 1H), 7.25 (s, 1H), 3.41 -3.31 (m, 1H),2.36 (s, 3H), 2.30 (s, 3H), 1.24 (d, J= 6.7 Hz, 6H). MS (m/z): 552.0 [M+1].

Reference： [1]Patent: WO2016/196644,2016,A1 .Location in patent: Paragraph 481; 482
[2]Patent: WO2018/102452,2018,A2 .Location in patent: Paragraph 465; 466
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4471 - 4477

15
{1-[3-chloro-6-(3-cyano-2-methoxymethoxyphenyl)cinnolin-4-yl]piperidin-4-yl}carbamic acid tert-butyl ester [ No CAS ]
[ 913836-14-3 ]
{1-[3-(3-chloro-5-methylphenyl)-6-(3-cyano-2-methoxymethoxyphenyl)cinnolin-4-yl]piperidin-4-yl}carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.4%	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In 1,4-dioxane; water; at 95 - 100℃; for 1h;Sealed tube; Inert atmosphere;	To a mixture of {1-[3-chloro-6-(3-cyano-2-methoxymethoxy-phenyl)-cinnolin-4-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester (50.0 mg, 0.0954 mmol), <strong>[913836-14-3]3-chloro-5-methylphenylboronic acid</strong> (19.5 mg, 0.114 mmol), Pd[t-Bu2P(4-NMe2C6H4)]2Cl2) (8.1 mg, 10 mol %), and K2CO3 (39.6 mg, 0.286 mmol) in a sealed tube was added dioxane (3 mL) and water (0.3 mL). The reaction mixture was bubbled with N2 (g) for 10 min and then heated at 100 C. for 30 min. Due to unreacted starting material, more <strong>[913836-14-3]3-chloro-5-methylphenylboronic acid</strong> (13.0 mg, 0.0763 mmol), Pd[t-Bu2P(4-NMe2C6H4)]2Cl2) (8.1 mg), and K2CO3 (39.6 mg) were added. After N2 (g) bubbling for 5 min, the reaction was continued to heat at 95 C. for additional 30 min. The mixture was concentrated and purified by silica gel column chromatography and C18 reversed-phase column chromatography (2nd purification). Pure fractions were combined, basified with saturated NaHCO3 (aq), and concentrated to remove MeCN. The aqueous residue was extracted with DCM (2*) and the combined organics were dried over anhydrous Na2SO4 and concentrated to dryness to afford the title compound (34.8 mg, 59.4% yield) as a brown solid. MS (M+H)+=614.3.

Reference： [1]Patent: US2018/16252,2018,A1 .Location in patent: Paragraph 1079

16
[ 17890-77-6 ]
[ 913836-14-3 ]
3-amino-6-(3-chloro-5-methylphenyl)pyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; for 5h;Reflux;	10 g of <strong>[17890-77-6]3-amino-6-bromopyrazine-2-carboxamide</strong> was added to 120 ml of tetrahydrofuran, 0.1 g of tetrakis(triphenylphosphine)palladium and 12.6 g of sodium carbonate were added, and then 14 g of 3-chloro-5-methyl was added. The phenylboronic acid was heated to reflux for 5 hours and concentrated. Water and ethyl acetate were added to extract and the mixture was separated. The organic phase was collected and concentrated. The residue was separated on a silica gel column to give 7 g of 3-amino-6-(3-chloro-5-methylphenyl)pyrazine-2-carboxamide

Reference： [1]Patent: CN107513041,2017,A .Location in patent: Paragraph 0020; 0027; 0028

17
N-(tert-butyl)-N-fluoro-2-methylbenzamide [ No CAS ]
[ 913836-14-3 ]
N-(tert-butyl)-2-(3-chloro-5-methylbenzyl)benzamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 13288 - 13292
Angew. Chem.,2018,p. 13472 - 13476,5

18
6-bromo-7-phenyl-1,8-naphthyridin-2(1H)-one [ No CAS ]
[ 913836-14-3 ]
6-(3-chloro-5-methylphenyl)-7-phenyl-1,8-naphthyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 18h;Inert atmosphere;	To a solution of 6-bromo-7-phenyl-1,8-naphthyridin-2(1H)-one (100 mg, 0.33 mmol, 1 eq.) in 1,4-dioxane (8 mL): water (2 mL) was added <strong>[913836-14-3]3-chloro-5-methylphenylboronic acid</strong> (41 mg, 0.33 mmol, 1.00 eq.), Na2CO3 (70 mg, 0.66 mmol, 2 eq.), PdCl2(dppf)DCM complex (6 mg, 0.008 mmol, 0.025 eq.). The reaction mixture was deoxygenated using N2 atmosphere and the reaction mixture was heated at 80 C. for 18 h. The reaction was monitored by NMR and LCMS. The reaction mixture was diluted with water (50 mL) and extracted using ethyl acetate (2*50 mL). The separated organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by reverse phase column chromatography to afford (20 mg, 17%) as a desired product. LCMS: ([M+1]+): 347. 1H NMR (400 MHz, DMSO-d6) delta 2.20 (s, 3H), 6.60 (d, 1H), 6.98-7.00 (d, 2H), 7.18 (s, 1H), 7.30-7.40 (s, 5H), 8.00 (s, 1H), 8.20 (s, 1H).

Reference： [1]Patent: US2019/23702,2019,A1 .Location in patent: Paragraph 0471-0473

19
6-(3-benzyloxyphenyl)-3-trifluoromethanesulfonyloxyquinoline-4-carboxylic acid methyl ester [ No CAS ]
[ 913836-14-3 ]
6-(3-benzyloxyphenyl)-3-(3-chloro-5-methyl-phenyl)quinoline-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
120 mg	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); water; potassium carbonate; In 1,4-dioxane; at 90℃; for 0.75h;Inert atmosphere;	to the dioxane solution (3 mL) of the oil from Step 1-3 (157 mg, 0.3 mmol) was added, followed by addition of 3-chloro-5-methyl-phenylboronic acid (102 mg, 0.6 mmol), K2C03 (83 mg, 0.6 mmol) and water (0.8 mL). The reaction mixture was bubbled with N2 for 5 min and then Pd(amphos)Cl2 was added and the mixture was stirred at 90C for 45 min. The reaction solution was concentrated and purified by silica gel chromatography eluted with hexane and ethyl acetate to afford the desired product (120 mg). MS (M+l)+: 494.5.

Reference： [1]Patent: WO2019/23278,2019,A1 .Location in patent: Paragraph 00240

20
benzyl (2S)-2-[(1-{6-[3-(benzyloxy)phenyl]-3-chloro-1,5-naphthyridin-4-yl}-N-methylformamido)methyl]pyrrolidine-1-carboxylate [ No CAS ]
[ 913836-14-3 ]
benzyl (2S)-2-[(1-{6-[3-(benzyloxy)phenyl]-3-(3-chloro-5-methylphenyl)-1,5-naphthyridin-4-yl}-N-methylformamido)methyl]pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66 mg	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In 1,4-dioxane; at 90℃; for 1.5h;Inert atmosphere; Sealed tube;	to the material from Step 4-3 (110 mg) in dioxane (2 ml), <strong>[913836-14-3]3-chloro-5-methylphenylboronic acid</strong> (105 mg, 0.62 mmol), K Chi. (82 mg, 0 6 mmol) were added. The mixture was bubbled with nitrogen for 5 min, then Pd (amphos)CI2 (1 1 mg, 0.016 mmol ) was added. It was sealed and heated at 90C for 90 min and then directly purified by silica gel column chromatography eluted with hexane/ethyl acetate to give the desired product as a brown solid (66 mg). MS (M+l)+: 711.6.

Reference： [1]Patent: WO2019/23278,2019,A1 .Location in patent: Paragraph 00259

21
1-(2-(difluoromethoxy)ethyl)naphthalene [ No CAS ]
[ 913836-14-3 ]
C₂₀H₁₇ClF₂O [ No CAS ]
C₂₀H₁₇ClF₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 6425 - 6429
Angew. Chem.,2019,vol. 131,p. 6491 - 6495,5

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[ CAS No. 913836-14-3 ] {[proInfo.proName]}

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[ 913836-14-3 ] Synthesis Path-Upstream 1~2

[ 913836-14-3 ] Synthesis Path-Downstream 1~21

Related Functional Groups of [ 913836-14-3 ]

Organoboron

Aryls

Chlorides

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[ 913836-14-3 ]