[ CAS No. 590418-05-6 ] {[proInfo.proName]}

Name: 590418-05-6|2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|97%
Brand: Ambeed
SKU: A179400
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Quality Control of [ 590418-05-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 590418-05-6 ]

SDS Specification

Alternatived Products of [ 590418-05-6 ]

Product Details of [ 590418-05-6 ]

CAS No. :	590418-05-6	MDL No. :	MFCD09033882
Formula :	C₁₃H₂₀BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BXTJBKJWBAHLEZ-UHFFFAOYSA-N
M.W :	233.11	Pubchem ID :	22559200
Synonyms :

Calculated chemistry of [ 590418-05-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	72.29
TPSA :	44.48 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 :	Yes
Log Kp (skin permeation) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.59
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	1.61
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.11
Solubility :	0.18 mg/ml ; 0.000772 mol/l
Class :	Soluble
Log S (Ali) :	-3.17
Solubility :	0.157 mg/ml ; 0.000672 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.03
Solubility :	0.0217 mg/ml ; 0.0000929 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.79

Safety of [ 590418-05-6 ]

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 [ 590418-05-6 ]

* 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 [ 590418-05-6 ]
Downstream synthetic route of [ 590418-05-6 ]

[ 590418-05-6 ] Synthesis Path-Upstream 1~2

1
[ 583-75-5 ]
[ 73183-34-3 ]
[ 590418-05-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; for 16 h; Inert atmosphere	Compound 13-2 (0405) To a mixture of 4-bromo-2-methylbenzenamine (500 mg, 2.69 mmol), KOAc (1.32 g, 13.4 mmol) and bis(pinacolato)diboron (2.05 mg, 8.0 mmol) in dioxane (4 mL) was added Pd(dppf)Cl₂(110 mg, 0.134 mmol). After having been degassed and recharged with nitrogen, the mixture was refluxed at 85° C. for 16 h. TLC showed that the reaction was complete. Water (20 mL) was added and the mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were dried over Na₂SO₄, filtered, concentrated and purified by silica gel column chromatography (DCM) to afford 13-2 as a white solid (485 mg, yield 77percent).
21%	With potassium acetate In dimethyl sulfoxide at 80℃; for 5 h; Inert atmosphere	Potassium acetate (317 mg, 3.22 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2- dioxaborolane) (300 mg, 1 .18 mmol) and 4-bromo-2-methyl-aniline (200 mg, 1 .08 mmol) were dissolved in DMSO (3 ml_). The reaction mixture was degassed using argon. 1 ,1 '-Bis- diphenylphosphine ferrocene palladium(ll) dichloride (24 mg, 0.03 mmol) was added and the reaction mixture was heated at 80 °C for 5 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 ml_). The organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (20 ml_). The organic layer was dried with sodium sulfate, filtered and purified by flash silica column chromatography (heptane:ethyl acetate, 0-40percent) to obtain a crude mixture of starting material and product. The mixture was purified using reversed phase column chromatography to obtain the title compound as a clear oil (50 mg, 21 percent).ESI-MS m/z: 234 (M+H)⁺.
21%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 5 h; Inert atmosphere	Potassium acetate (317 mg, 3.22 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (300 mg, 1.18 mmol) and 4-bromo-2-methyl-aniline (200 mg, 1.08 mmol) were dissolved in dimethylsulfoxide (3 mL). The reaction mixture was degassed using argon. 1,1'-Bis-diphenylphosphine ferrocene palladium(II) dichloride (24 mg, 0.03 mmol) was added and the reaction mixture was heated at 80 °C for 5 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (20 mL). The organic layer was dried with sodium sulfate, filtered and purified by flash silica column chromatography (heptane:ethyl acetate, 0-40percent) to obtain a crude mixture of starting material and product. The mixture was purified using reversed phase column chromatography to obtain the title compound as a clear oil (50 mg, 21percent). ESI-MS m/z: 234 (M+H)⁺.

Reference： [1] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 291
[2] Patent: WO2012/104305, 2012, A1, . Location in patent: Page/Page column 150
[3] Patent: EP3034078, 2016, A1, . Location in patent: Paragraph 0241-0242
[4] Patent: US2005/171131, 2005, A1, . Location in patent: Page/Page column 54-55
[5] Patent: US2006/25383, 2006, A1, . Location in patent: Page/Page column 54
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2326 - 2349

2
[ 590418-04-5 ]
[ 590418-05-6 ]

Reference： [1] Patent: US2004/44258, 2004, A1, . Location in patent: Page 157

[ 590418-05-6 ] Synthesis Path-Downstream 1~18

1
[ 590418-04-5 ]
[ 590418-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;platinum(IV) oxide; In methanol; at 20.0℃; for 0.5h;	A solution of Intermediate 102 (4.20 g) in methanol (100 ml) was added with platinum oxide (50 mg, Ald) and stirred at room temperature for 30 minutes under a hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate 103, 2.81 g). Mass (LCMS): 234 (M++1), retention time: 3.04 minutes (elution condition: B).

Reference： [1]Patent: US2004/44258,2004,A1 .Location in patent: Page 157

2
[ 583-75-5 ]
[ 73183-34-3 ]
[ 590418-05-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 85.0℃; for 16.0h;Inert atmosphere;	Compound 13-2 (0405) To a mixture of 4-bromo-2-methylbenzenamine (500 mg, 2.69 mmol), KOAc (1.32 g, 13.4 mmol) and bis(pinacolato)diboron (2.05 mg, 8.0 mmol) in dioxane (4 mL) was added Pd(dppf)Cl2 (110 mg, 0.134 mmol). After having been degassed and recharged with nitrogen, the mixture was refluxed at 85 C. for 16 h. TLC showed that the reaction was complete. Water (20 mL) was added and the mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (DCM) to afford 13-2 as a white solid (485 mg, yield 77%).
21%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 5.0h;Inert atmosphere;	Potassium acetate (317 mg, 3.22 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2- dioxaborolane) (300 mg, 1 .18 mmol) and 4-bromo-2-methyl-aniline (200 mg, 1 .08 mmol) were dissolved in DMSO (3 ml_). The reaction mixture was degassed using argon. 1 ,1 '-Bis- diphenylphosphine ferrocene palladium(ll) dichloride (24 mg, 0.03 mmol) was added and the reaction mixture was heated at 80 C for 5 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 ml_). The organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (20 ml_). The organic layer was dried with sodium sulfate, filtered and purified by flash silica column chromatography (heptane:ethyl acetate, 0-40%) to obtain a crude mixture of starting material and product. The mixture was purified using reversed phase column chromatography to obtain the title compound as a clear oil (50 mg, 21 %).ESI-MS m/z: 234 (M+H)+.
21%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80.0℃; for 5.0h;Inert atmosphere;	Potassium acetate (317 mg, 3.22 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (300 mg, 1.18 mmol) and 4-bromo-2-methyl-aniline (200 mg, 1.08 mmol) were dissolved in dimethylsulfoxide (3 mL). The reaction mixture was degassed using argon. 1,1'-Bis-diphenylphosphine ferrocene palladium(II) dichloride (24 mg, 0.03 mmol) was added and the reaction mixture was heated at 80 C for 5 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (20 mL). The organic layer was dried with sodium sulfate, filtered and purified by flash silica column chromatography (heptane:ethyl acetate, 0-40%) to obtain a crude mixture of starting material and product. The mixture was purified using reversed phase column chromatography to obtain the title compound as a clear oil (50 mg, 21%). ESI-MS m/z: 234 (M+H)+.

	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 92.0℃; for 3.0h;	A mixture of 4-bromo-2-methyl-phenylamine (372 mg, 2 mmol), bis(pinacolato)diboron (508 mg, 2 mmol), PdCl2dppf (82 mg, 0.1 mmol), and KOAc (493 mg, 5 mmol) in 1,4-dioxane was heated at 92 C. for 3 h. The reaction mixture was partitioned between EtOAc and water and the organic extract was concentrated and purified by column chromatography to give the titled 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (350 mg, 76%).
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80.0℃; for 15.0h;	Preparation #4: 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine A mixture of 4-bromo-2-methylaniline (0.250 g, 1.34 mmol), bis(pinacolato)diboron (0.442 g, 1.747 mmol), dichloro[1,1'bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (0.110 g, 0.134 mmol), and potassium acetate (0.329 g, 3.357 mmol) was heated in N,N-dimethylformamide (5 mL) at about 80 C. for about 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and was purified by flash column chromatography on silica gel using ethyl acetate/heptane (3:7) as the mobile phase to give 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine as a yellow oil (0.213 g, 0.914 mmol); RP-HPLC (25% to 100% acetonitrile/0.1 M aqueous ammonium acetate, buffered to pH 4.5, over 10 min at 1.0 mL/min; lambda=254 nm; Hypersil C18, 100 A, 5 mum, 250*4.6 mm column) Rt 11.02 min.

Reference： [1]Patent: CN110627775,2019,A .Location in patent: Paragraph 0194-0197
[2]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 291
[3]Patent: WO2012/104305,2012,A1 .Location in patent: Page/Page column 150
[4]Patent: EP3034078,2016,A1 .Location in patent: Paragraph 0241-0242
[5]Patent: US2005/171131,2005,A1 .Location in patent: Page/Page column 54-55
[6]Patent: US2006/25383,2006,A1 .Location in patent: Page/Page column 54
[7]Journal of Medicinal Chemistry,2015,vol. 58,p. 2326 - 2349

3
[ 861103-60-8 ]
[ 590418-05-6 ]
5-(4-amino-3-methyl-phenyl)-6-ethyl-pyrimidine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120.0℃; for 0.333333h;Microwave;	To a mixture of boronate from Example 147B (124 mg, 0.5 mmol), 5-bromo-6-ethyl-pyrimidine-2,4-diamine from Example 147A (88 mg, 0.4 mmol), Pd(Ph3)4 (23 mg, 0.02 mmol) in toluene (1 mL) was added EtOH (0.4 mL) and K2CO3aq (3 M, 0.5 mL, 1.5 mmol). The mixture was heated at 120 C. under microwave irradiation for 20 min. The mixture was extracted with EtOAc and the organic extract was concentrated and purified by column chromatography to give 5-(4-amino-3-methyl-phenyl)-6-ethyl-pyrimidine-2,4-diamine (70 mg, 72%).

Reference： [1]Patent: US2005/171131,2005,A1 .Location in patent: Page/Page column 55

Yield	Reaction Conditions	Operation in experiment
50%		General procedure: Step 3-Preparation of 3-aminophenylboronic acid pinacolate ester (2-(3-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane; Compound 6) from 3-aminophenylboronic acid hydrogen sulphate salt solution of Example 2. [0054] 1 V of Toluene was added to 300 g of 3-aminophenylboronic acid hydrogen sulphate salt solution (obtained at *point 1 of the previous example and containing about 202 mmoles of product) and, under stirring, the pH value of this mixture was corrected to a final pH value of 8,0 with NaOH 33%. 1 eq. Of Pinacol was added and the obtained reaction mixture maintained under stirring at room temperature until the conversion was complete. The organic phase was separated and evaporated under vacuum to residue. 1V of Heptane was added and the obtained slurry maintained under stirring at 20-25C for 1 hour to afford a precipitate that was recovered by filtration and dried under vacuum (200 mmHg) at 40C for 8 hours to give 36,5 g of compound 6 (169 mmoles; 84 % yields). [0055] Overall molar yields from Benzophenone (without isolation of intermediate compound 5): 61%
50%	With sodium hydroxide; In water; at 20.0℃;pH 8.0;	General procedure: Step 3Preparation of 3 -aminophenylboronic acid pinacolate ester (2- ( 3 -bromophenyl) -4 , 4 , 5 , 5- tetramethyl-1, 3 , 2 -Dioxaborolane ; Compound 6) from 3- aminophenylboronic acid hydrogen sulphate salt solution of Example 2IV of Toluene was added to 300 g of 3~ aminophenylboronic acid hydrogen sulphate salt solution (obtained at *point 1 of the previous example and containing about 202 mmoles of product) and, under stirring, the pH value of this mixture was corrected to a final pH value of 8,0 with NaOH 33%. 1 eq. Of Pinacol was added and the obtained reaction mixture maintained under stirring at room temperature until the conversion was complete. The organic phase was separated and evaporated under vacuum to residue. IV of Heptane was added and the obtained slurry maintained under stirring at 20-25C for 1 hour to afford a precipitate that was recovered by filtration and dried under vacuum (200 mmHg) at 40C for 8 hours to give 36,5 g of compound 6 {169 mmoles; 84 % yields) . Overall molar yields from Benzophenone (without isolation of intermediate compound 5) : 61%
0.992 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 85.0℃; for 4.5h;Inert atmosphere;	General procedure: 2.1: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 5.0 g (21.1 mmol) of 2-fluoro-4-iodoaniline and 5.89 g (23.2 mmol) of bis(pinacolato)diborane are dissolved in 130 ml of DMSO. 6.21 g (63.3 mmol) of potassium actetate are added and argon is bubbled through for 10 min. 1.21 g (1.50 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complexed with dichloromethane (1:1), is added and the mixture is heated at 85 C. for 4.5 hours, under argon, and then cooled and diluted with 500 ml of water. The mixture is extracted with ethyl acetate (3*200 ml), the organic phases are washed with water, dried over Na2SO4 and then evaporated to dryness. The crude product is purified by chromatography on silica (eluent: cyclohexane/ethyl acetate 90/10). 3.73 g of product are obtained in the form of a white powder. Yield=75%. Melting point: 112 C. 1H NMR (400 MHz; CDCl3): delta (ppm): 1.2 (s; 12H); 3.8 (br s; 2H); 6.55 (t; 1H; 7 Hz); 7.25-7.35 (m; 2H).

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; at 80.0℃; for 16.0h;Inert atmosphere;

General procedure: To a solution of isopropyl N-[4-[5-[4-bromo-2-(tert-butylsulfamoyl)phenyl] thiazol-2- yl]phenyl]carbamate (100.00 mg, 181.00 muiotaetaomicron, 1.00 eq.) in dioxane (3.00 mL) was added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 1,3,2-dioxaborolane (183.85 mg, 724.00 muetaomicron, 4.00 eq.), Na2C03 (38.37 mg, 362.00 muetaomicron, 2.00 (0309) eq.) and Pd(dppf)Cl2.CH2Cl2 (14.78 mg, 18.10 muiotaetaomicron, 0.10 eq.) and the mixture was stirred at 80C under N2 for 16 hrs. LCMS showed the reaction was complete. The mixture was diluted with water (30 mL) and extracted with EtOAc (30mL X 3). The combined organic phase was dried, filtered and concentrated. The residue was purified by prep-TLC (0310) (PE:EtOAc=2: l) to giv intermediate compound 34 (90.00 mg, 150.11 muetaomicron, 82.93% yield) as a yellow solid. ESI [M+H] =600.3

5
[ 590418-05-6 ]
C₂₅H₂₈N₄O₅S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2326 - 2349

6
[ 590418-05-6 ]
[ 1009622-61-0 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2326 - 2349

7
[ 590418-05-6 ]
[ 1009627-11-5 ]
N-methyl-4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]aniline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2326 - 2349

8
[ 3034-53-5 ]
[ 590418-05-6 ]
C₁₀H₁₀N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 85.0℃; for 11.0h;Inert atmosphere;	Compound 13-3 (0406) To a mixture of 13-2 (257 mg, 1.57 mmol), K2CO3 (653 mg, 4.7 mmol) and 2-bromothiazole (367 mg, 1.57 mmol) in the mixed solvent (Dioxane/H2O=2/1, 15 mL) was added Pd(PPh3)4 (182 mg, 0.157 mmol). After having been degassed and recharged with nitrogen, the mixture was refluxed at 85 C. for 11 h. TLC showed that the reaction was complete. Water (10 mL) was added and the mixture was extracted with ethyl acetate (20 mL×3). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:Acetone=10:1) to afford 13-3 as a yellow oil (229 mg, yield 76%).

Reference： [1]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 291

9
[ 590418-05-6 ]
[ 1371629-28-5 ]

Reference： [1]Patent: EP3034078,2016,A1

10
[ 590418-05-6 ]
potassium 8-(3-methyl-4-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate [ No CAS ]

Reference： [1]Patent: EP3034078,2016,A1

11
[ 590418-05-6 ]
[ 1371629-97-8 ]
[ 1371630-16-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,2-dimethoxyethane; water; at 90.0℃; for 1.0h;Inert atmosphere;	General procedure: [0156] The quinolizine scaffold (1 eq.), boronate (1.3 eq.)and cesium carbonate (3 eq.) were added to a 3:1 mixtureof 1,2-dimethoxyethane and water. Themixture was degassed with argon. 1,1?-Bis-diphenylphosphine ferrocenepalladium(II) dichloride (0.1 eq.) was added andthe mixture was heated at 90 C under an argon atmosphere for 1h. Thereaction mixture was cooled. Themixture was diluted with CH2Cl2 (3 mL) and water was added (3 mL). The layers wereseparated using a phase separator andthe aqueous layer was extracted with CH2Cl2 (2 x 5 mL). The combined organiclayers were dried over sodium sulfateand concentrated in vacuo. The crude productwas purified by flash silica columnchromatography and dried in vacuo to afford the desiredproduct. Methyl 8-(4-amino-3-methyl-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (50 mg, 0.17 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline (52 mg, 0.22 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (31 mg, 50%). ESI-MS m/z: 363 (M+H)+.

Reference： [1]Patent: EP3034078,2016,A1 .Location in patent: Paragraph 0156; 0243-0244

12
3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine [ No CAS ]
[ 590418-05-6 ]
3-(4-amino-3-methylphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 11398 - 11414

13
[ 590418-05-6 ]
[ 78060-56-7 ]
2-methyl-4-(6-(trifluoromethyl)quinolin-2-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 90.0℃; for 3.0h;	Over a solution of 2-chloro-6-(trifluoromethyl)quinoline (20 g, 86.36 mmol, 1.00 equiv) and 2-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (24 g, 102.95 mmol, 1.20 equiv) in ethylene glycol dimethyl ether (400 mL) and water (80 mL), sodium carbonate (27.4 g, 258.51 mmol, 3.00 equiv) and Pd(PPh3)4 (5 g, 4.33 mmol, 0.05 equiv) were added. The resulting solution was stirred for 3 h at 90C and the reaction quenched by addition of 200 mL of water. Extraction with ethyl acetate(3x200 mL) followed by evaporation of volatiles under reduced pressure afforded a residue that was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 :5) to afford the desired product as a yellow solid in 67% yield.

Reference： [1]Patent: WO2019/18562,2019,A1 .Location in patent: Paragraph 0231

14
[ 590418-05-6 ]
methyl 6-(3-methyl-4-propionamidophenyl)nicotinate [ No CAS ]

Reference： [1]Patent: WO2019/213570,2019,A1

15
[ 590418-05-6 ]
methyl 6-(3-methyl-4-(N-methylpropionamido)phenyl)nicotinate [ No CAS ]

Reference： [1]Patent: WO2019/213570,2019,A1

16
[ 590418-05-6 ]
6-(3-methyl-4-(N-methylpropionamido)phenyl)nicotinic acid [ No CAS ]

Reference： [1]Patent: WO2019/213570,2019,A1

17
[ 590418-05-6 ]
6-(3-methyl-4-(N-methylpropionamido)phenyl)-N-(pyridin-3-ylmethyl)nicotinamide [ No CAS ]

Reference： [1]Patent: WO2019/213570,2019,A1

18
[ 26218-78-0 ]
[ 590418-05-6 ]
methyl 6-(4-amino-3-methylphenyl)nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; dichloromethane; water; at 70.0℃;Inert atmosphere;	To a solution of <strong>[590418-05-6]2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (200 mg, 0.858 mmol) and methyl 6-bromopyridine-3-carboxylate (271 mg, 1.25 mmol) in a mixture of 1,4-dioxane (13 mL) and water (3 mL), was added K3PO4 (728 mg, 3.43 mmol). The reaction mixture was degassed with Argon for 5 min when Pd(dppf)Cl2xDCM (49 mg, 0.0601 mmol) was added. The reaction mixture was heated to 70 C and stirred overnight. After cooling to room temperature, the organic layer was concentrated under reduced pressure. The remaining residue was dissolved in EtOAC (50 mL), and washed with a saturated solution of NaHCO3 and brine. The organic layer was concentrated under reduced pressure to afford methyl 6-(4-amino-3-methylphenyl)nicotinate (105 mg, 45%). LC-MS (Method 2): Rt = 0.93 min; m/z= 243.07 (M+H)+.

Reference： [1]Patent: WO2019/213570,2019,A1 .Location in patent: Paragraph 0331; 0758-0760

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[ 590418-05-6 ]

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[ CAS No. 590418-05-6 ] {[proInfo.proName]}

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[ 590418-05-6 ] Synthesis Path-Upstream 1~2

[ 590418-05-6 ] Synthesis Path-Downstream 1~18

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Organoboron

Aryls

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[ 590418-05-6 ]