[ CAS No. 152849-72-4 ]

Name: 152849-72-4|Methyl 5-bromo-2,4-dimethylbenzoate|95%
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Quality Control of [ 152849-72-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 152849-72-4 ]

Product Details of [ 152849-72-4 ]

CAS No. :	152849-72-4	MDL No. :	MFCD11112985
Formula :	C₁₀H₁₁BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DVWSCROTFQAIEU-UHFFFAOYSA-N
M.W :	243.10	Pubchem ID :	10014652
Synonyms :

Calculated chemistry of [ 152849-72-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.35
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.74
Log Po/w (XLOGP3) :	3.2
Log Po/w (WLOGP) :	2.85
Log Po/w (MLOGP) :	3.25
Log Po/w (SILICOS-IT) :	3.33
Consensus Log Po/w :	3.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.57
Solubility :	0.065 mg/ml ; 0.000267 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0915 mg/ml ; 0.000377 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.11
Solubility :	0.019 mg/ml ; 0.0000782 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 152849-72-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 152849-72-4 ]

* 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 [ 152849-72-4 ]
Downstream synthetic route of [ 152849-72-4 ]

[ 152849-72-4 ] Synthesis Path-Upstream 1~2

1
[ 67-56-1 ]
[ 842136-27-0 ]
[ 152849-72-4 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 23, p. 7099 - 7107

2
[ 842136-27-0 ]
[ 152849-72-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1939, vol. 58, p. 218,224

[ 152849-72-4 ] Synthesis Path-Downstream 1~39

1
[ 842136-27-0 ]
[ 152849-72-4 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1939,vol. 58,p. 218,224

2
[ 152849-72-4 ]
3-bromo-4,6-dimethyl-2,5-dinitro-benzoic acid methyl ester [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1939,vol. 58,p. 218,224

3
[ 152849-72-4 ]
[ 151859-36-8 ]
C₁₄₉H₁₇₉BrO₇ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1993,vol. 115,p. 10688 - 10694

4
[ 67-56-1 ]
[ 842136-27-0 ]
[ 152849-72-4 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7099 - 7107

5
[ 152849-72-4 ]
[ 151160-12-2 ]
[ 159217-49-9 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7099 - 7107

6
[ 7664-93-9 ]
[ 152849-72-4 ]
[ 7697-37-2 ]
3-bromo-4,6-dimethyl-2,5-dinitro-benzoic acid methyl ester [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1939,vol. 58,p. 218,224

7
[ 615-87-2 ]
chromic acid [ No CAS ]
[ 152849-72-4 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7099 - 7107

8
[ 152849-72-4 ]
[ 151859-36-8 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7099 - 7107

9
[ 152849-72-4 ]
[5-(Bis-{5-[bis-(4-tert-butyl-phenyl)-methoxy-methyl]-2,4-dimethyl-phenyl}-methoxy-methyl)-2,4-dimethyl-phenyl]-bis-(4-tert-butyl-phenyl)-methanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7099 - 7107

10
[ 152849-72-4 ]
1-(2-(difluoromethoxy)phenyl)piperidin-4-amine [ No CAS ]
methyl 5-(1-(2-(difluoromethoxy)phenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49.92%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In toluene; at 90.0℃; for 16.0h;	Step 3: methyl 5-(1-(2-(difluoromethoxy)phenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate 1-[2-(difluoromethoxy)phenyl]piperidin-4-amine (240 mg, 990 umol), methyl 5-bromo-2,4-dimethyl-benzoate (240 mg, 990 umol), Pd2(dba)3 (54 mg, 59 umol), BrettPhos (73 mg, 118 umol), Cs2CO3 (450 mg, 1 mmol) in toluene (5 mL) was stirred at 90 C. for 16 h. The mixture was filtered by celite, the filtrate was concentrated and was purified via silica gel chromatography eluting with PE/EA from 50/1 to 20/1 to obtain methyl 5-[[1-[2-(difluoromethoxy)phenyl]-4-piperidyl]amino]-2,4-dimethyl-benzoate (200 mg, 49.92%) as white solid. ESI-MS (EI+, m/z): 405 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 1426; 1423

11
[ 152849-72-4 ]
2-(4-aminopiperidin-1-yl)-3,5-difluorobenzonitrile [ No CAS ]
methyl 5-(1-(2-cyano-4,6-difluorophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39.60%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In toluene; for 16.0h;	Step 3: methyl 5-(1-(2-cyano-4,6-difluorophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate A solution of 2-(4-amino-1-piperidyl)-3,5-difluoro-benzonitrile (120 mg, 505 umol), methyl 5-bromo-2,4-dimethyl-benzoate (122 mg, 505 umol), Pd2(dba)3 (27 mg, 30 umol), BrettPhos (37 mg, 60 umol), Cs2CO3 (230 mg, 708 umol) in toluene (5 mL) was stirred at 100 C. for 16 h. Filtered and concentrated, the crude product was purified via silica gel chromatography to obtain methyl 5-[[1-(2-cyano-4,6-difluoro-phenyl)-4-piperidyl]amino]-2,4-dimethyl-benzoate (80 mg, 39.60%) as yellow solid. ESI-MS (EI+, m/z): 400 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 1440; 1437

12
[ 152849-72-4 ]
2-(4-amino-3-methyl-1-piperidyl)benzonitrile [ No CAS ]
methyl 5-[[1-(2-cyanophenyl)-3-methyl-4-piperidyl]amino]-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30.67%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; sodium t-butanolate; at 80.0℃;	Step 4: Methyl 5-[[1-(2-cyanophenyl)-3-methyl-4-piperidyl]amino]-2,4-dimethyl-benzoate A mixture of 2-(4-amino-3-methyl-1-piperidyl)benzonitrile (410.00 mg, 1.90 mmol), methyl 5-bromo-2,4-dimethyl-benzoate (461.89 mg, 1.90 mmol), tBuONa (273.60 mg, 2.85 mmol), Pd2(dba)3 (34.81 mg, 38.00 umol) and BrettPhos (40.81 mg, 76.00 umol) in toluene (15.00 mL) was stirred at 80 C. for 17 h. The mixture was filtered and purified by SGC to afford methyl 5-[[1-(2-cyanophenyl)-3-methyl-4-piperidyl]amino]-2,4-dimethyl-benzoate (220.00 mg, 582.81 umol, 30.67% yield) as product. ESI-MS (EI+, m/z): 378.3 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0902; 0897; 1342; 1338

13
[ 152849-72-4 ]
2-(3-aminopyrrolidin-1-yl)benzonitrile [ No CAS ]
methyl 5-(1-(2-cyanophenyl)pyrrolidin-3-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; sodium t-butanolate; In toluene; at 80.0℃;Inert atmosphere;	Step 2: methyl 5-(1-(2-cyanophenyl)pyrrolidin-3-ylamino)-2,4-dimethylbenzoate A mixture of 2-(3-aminopyrrolidin-1-yl)benzonitrile (385.00 mg, 2.06 mmol), methyl 5-bromo-2,4-dimethyl-benzoate (500.79 mg, 2.06 mmol), Pd2(dba)3 (94.32 mg, 103.00 umol), BrettPhos (110.57 mg, 206.00 umol), and sodium tert-butoxide (395.93 mg, 4.12 mmol) in toluene (30.00 mL) was heated at 80 C. under N2 atmosphere for 6 h. The reaction mixture was concentrated and purified via preparative HPLC to afford methyl 5-[[1-(2-cyanophenyl)pyrrolidin-3-yl]amino]-2,4-dimethyl-benzoate (540.00 mg, 1.55 mmol, 75% yield) as a slight oil. ESI-MS (EI+, m/z): 350.0 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 1033; 1030

14
[ 152849-72-4 ]
1-(2-(trifluoromethoxy)phenyl)piperidin-4-amine [ No CAS ]
methyl 2,4-dimethyl-5-(1-(2-trifluoromethoxyphenyl)piperidin-4-yl-amino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.04%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In toluene; at 90.0℃; for 16.0h;	Step 3: methyl 2,4-dimethyl-5-(1-(2-trifluoromethoxyphenyl)piperidin-4-yl-amino)benzoate 1-[2-(trifluoromethoxy)phenyl]piperidin-4-amine (276 mg, 1.06 mmol), methyl 5-bromo-2,4-dimethyl-benzoate (257 mg, 1.06 mmol), Pd2(dba)3 (58 mg, 63 umol), BrettPhos (79 mg, 127 umol), Cs2CO3 (482 mg, 1.48 mmol) in toluene (10 mL) was stirred at 90 C. for 16 h. The mixture was filtered through celite, H2O (50 mL) was added, then extracted with EtOAc (50 mL*3), combined the organic layers, concentrated to give a residue which was purified by flash column (PE/EA=7/3) to afford methyl 2,4-dimethyl-5-(1-(2-(trifluoromethoxy)phenyl)piperidin-4-ylamino)benzoate (242 mg, 54.04%) as a pale white solid. ESI-MS (EI+, m/z): 423 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 1418; 1415

15
[ 152849-72-4 ]
2-(4-aminopiperidin-1-yl)-3-fluorobenzonitrile hydrochloride [ No CAS ]
methyl 5-(1-(2-cyano-6-fluorophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In 1,4-dioxane; at 110.0℃; for 17.0h;	Step 3: Methyl 5-(1-(2-cyano-6-fluorophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate A mixture of 2-(4-amino-1-piperidyl)-3-fluoro-benzonitrile (1.50 g, 6.84 mmol), methyl 5-bromo-2,4-dimethyl-benzoate (1.39 g, 5.70 mmol), tris(dibenzylideneacetone)dipalladium(0) (522.05 mg, 570.00 umol), dicyclohexyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (612.02 mg, 1.14 mmol), cesium carbonate (5.57 g, 17.10 mmol) and dioxane (20.00 mL) was stirred at 110 C. for 17 h. The reaction mixture was cooled down to rt, filtered, and concentrated to give a residue which was purified by a flash column (5% to 10% of EtOAc in PE) to afford methyl 5-[[1-(2-cyano-6-fluoro-phenyl)-4-piperidyl]amino]-2,4-dimethyl-benzoate (1.80 g, 83% yield) as a red solid. ESI-MS (EI+, m/z): 382.2 [M+H]+

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0723; 0719

16
[ 152849-72-4 ]
C₁₁H₁₅ClN₂ [ No CAS ]
C₂₁H₂₅ClN₂O₂ [ No CAS ]

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0906; 0911; 0916

17
[ 891854-16-3 ]
[ 152849-72-4 ]
methyl 5-(1-(3-cyanophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 80.0℃; for 5.0h;	Step 1: Methyl 5-(1-(3-cyanophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate The procedure for methyl 5-(1-(3-cyanophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate was the same as example 32. ESI-MS (EI+, m/z): 364.1 [M+H]+

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0987; 0985

18
[ 891854-16-3 ]
[ 152849-72-4 ]
5-(1-(3-cyanophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoic acid [ No CAS ]

Reference： [1]Patent: US2018/127370,2018,A1

19
[ 152849-72-4 ]
2-(4-amino-3,3-dimethylpiperidin-1-yl)benzonitrile [ No CAS ]
methyl 5-(1-(2-cyanophenyl)-3,3-dimethylpiperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; sodium t-butanolate; In toluene; for 17.0h;	Step 4: Methyl 5-(1-(2-cyanophenyl)-3,3-dimethylpiperidin-4-ylamino)-2,4-dimethylbenzoate 2-(4-amino-3,3-dimethyl-1-piperidyl)benzonitrile (100.00 mg, 436.07 umol), methyl 5-bromo-2,4-dimethyl-benzoate (116.61 mg, 479.68 umol), tBuONa (83.81 mg, 872.14 umol), BrettPhos (46.81 mg, 87.21 umol), and Pd2(dba)3 (199.72 mg, 218.04 umol) were dissolved in toluene (5.00 mL) and the mixture was stirred at 85 C for 17 h. The mixture was purified by column chromatography (PE/EA=10/1) to afford methyl 5-[[1-(2-cyanophenyl)-3,3-dimethyl-4-piperidyl]amino]-2,4-dimethyl-benzoate (30.00 mg, 76.63 umol, 17%) as a yellow oil. ESI-MS (EI+, m/z): 392.0 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0670; 0665

20
[ 152849-72-4 ]
C₂₀H₂₃ClN₂O₂ [ No CAS ]

Reference： [1]Patent: US2018/127370,2018,A1

21
[ 152849-72-4 ]
2-(4-(5-(1-(2-chlorophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoyl)piperazin-1-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: US2018/127370,2018,A1

22
[ 1039022-11-1 ]
[ 152849-72-4 ]
5-[1-(2-cyanophenyl)piperidin-4-yl]amino}-2,4-dimethylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.33%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; sodium t-butanolate; In toluene; at 80.0℃; for 16.0h;Inert atmosphere;	Step 2: 5-(1-(2-Cyanophenyl) piperidin-4-ylamino)-2,4-dimethylbenzoic acid To a solution of methyl 5-bromo-2,4-dimethyl-benzoate (920.00 mg, 3.78 mmol), 2-(4-amino-1-piperidyl)benzonitrile (989.04 mg, 4.91 mmol) in toluene (20.00 mL) was added BrettPhos (284.05 mg, 529.20 umol), Pd2(dba)3 (242.30 mg, 264.60 umol) and sodium tert-butoxide (1.09 g, 11.34 mmol) under nitrogen. The reaction mixture was stirred at 80 C. for 16 h. then cooled to rt and diluted with H2O (100 mL). The pH was adjusted to 4 to 5 with 1 N HCl and then extracted with EtOAc (80 mL*3). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to obtain the crude product, which was purified by chromatography (silica, ethyl acetate/petroleum ether=1/3) to afford the desired product 5-[[1-(2-cyanophenyl)-4-piperidyl]amino]-2,4-dimethyl-benzoic acid (1.10 g, 3.15 mmol, 83.33% yield) as a solid. ESI-MS (EI+, m/z): 350.2 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0970; 0967

23
2-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)benzonitrile [ No CAS ]
[ 152849-72-4 ]
methyl 5-(3-(2-cyanophenyl)-3-azabicyclo[3.1.0]hexan-6-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.78%	With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; sodium t-butanolate; In toluene;	Step 2: Methyl 5-(3-(2-cyanophenyl)-3-azabicyclo[3.1.0]hexan-6-ylamino)-2,4-dimethylbenzoate A mixture of 2-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)benzonitrile (20.00 mg, 100.38 umol), methyl 5-bromo-2,4-dimethyl-benzoate (24.40 mg, 100.38 umol), tBuONa (14.45 mg, 150.56 umol), Pd2(dba)3 (1.84 mg, 2.01 umol) and BrettPhos (2.16 mg, 4.02 umol) in toluene (5.00 mL) was stirred at 80 C. for 17 h. The mixture was filtered and purified by SGC to get methyl 5-[[3-(2-cyanophenyl)-3-azabicyclo[3.1.0]hexan-6-yl]amino]-2,4-dimethyl-benzoate (5.00 mg, 13.83 umol, 13.78% yield) as product. ESI-MS (EI+, m/z): 362.2 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0880; 0877

24
[ 152849-72-4 ]
1-(3-methoxyphenyl)piperidin-4-amine [ No CAS ]
methyl 5-(1-(3-methoxyphenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100.0℃; for 17.0h;	Step 3: Methyl 5-(1-(3-methoxyphenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate A mixture of 1-(3-methoxyphenyl) piperidin-4-amine (100.00 mg, 484.78 umol), methyl 5-bromo-2,4-dimethyl-benzoate (117.85 mg, 484.78 umol), BINAP (60.37 mg, 96.96 umol), Cs2CO3 (315.90 mg, 969.56 umol) and Pd2(dba)3 (88.81 mg, 96.96 umol) in dioxane (5.00 mL) was stirred at 100 C. for 17 h. The mixture was purified by column chromatography (PE/EA=5/1) to give methyl 5-[[1-(3-methoxyphenyl)-4-piperidyl]amino]-2,4-dimethyl-benzoate (50.00 mg, 135.70 umol, 28%) as a yellow oil. ESI-MS (EI+, m/z): 369.3 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0692; 0688

25
1-(2-methoxyphenyl)piperidin-4-amine [ No CAS ]
[ 152849-72-4 ]
methyl 5-(1-(2-methoxyphenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.87%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 90.0℃;Inert atmosphere;	Step 3: Methyl 5-(1-(2-methoxyphenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate A mixture of methyl 5-bromo-2,4-dimethyl-benzoate (785.66 mg, 3.23 mmol), 1-(2-methoxyphenyl)piperidin-4-amine (800.00 mg, 3.88 mmol) in toluene (25.00 mL) was added BINAP (201.24 mg, 323.19 umol) and sodium tert-butoxide (621.16 mg, 6.46 mmol). The mixture was degassed for 3 mins, then, Pd2 (dba)3 (295.95 mg, 323.19 umol) was added. The resulting mixture was degassed for 3 mins. After that, the mixture was kept stirring at 90 C. for 18 h under N2. The mixture was diluted with EtOAc (60 mL), filtrated and concentrated in vacuo, the residue was purified by CombiFlash (UV254, silica gel, 40 g, EA/PE from 0% to 40% to give the desired product methyl 5-[[1-(2-methoxyphenyl)-4-piperidyl]amino]-2,4-dimethyl-benzoate (189.00 mg, 512.93 umol, 15.87% yield) as a yellow solid. ESI-MS (EI+, m/z): 369.3 [M+H]+. 1H NMR (500 MHz, MeOD-d4) delta 7.24 (s, 1H), 7.08-7.01 (m, 2H), 6.99-6.95 (m, 2H), 6.93 (td, J=7.6, 1.5 Hz, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.52-3.40 (m, 3H), 2.78 (td, J=11.8, 2.1 Hz, 2H), 2.43 (s, 3H), 2.19 (s, 3H), 2.16 (d, J=12.6 Hz, 2H), 1.73 (td, J=14.3, 3.6 Hz, 2H).

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 1063; 1059

26
[ 152849-72-4 ]
2-[(3S)-4-(5-[1-(2-cyanophenyl)piperidin-4-ylidene]methyl}-2,4-dimethylbenzoyl)-3-methylpiperazin-1-yl]benzene-1-sulfonamide [ No CAS ]