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[ CAS No. 214360-63-1 ] {[proInfo.proName]}

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Chemical Structure| 214360-63-1
Chemical Structure| 214360-63-1
Structure of 214360-63-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 214360-63-1 ]

CAS No. :214360-63-1 MDL No. :MFCD22414466
Formula : C14H21BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :KMHWSWITVAWIEB-UHFFFAOYSA-N
M.W : 248.13 Pubchem ID :21923912
Synonyms :

Calculated chemistry of [ 214360-63-1 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 74.38
TPSA : 27.69 Ų

Pharmacokinetics

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

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.24
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0725 mg/ml ; 0.000292 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0794 mg/ml ; 0.00032 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.52
Solubility : 0.00755 mg/ml ; 0.0000304 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.92

Safety of [ 214360-63-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 214360-63-1 ]

* 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.

  • Downstream synthetic route of [ 214360-63-1 ]

[ 214360-63-1 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 214360-63-1 ]
  • 4-(2-cyanoethyl)-2-methylphenyl trifluoromethanesulfonate [ No CAS ]
  • 3-(4'-methoxy-2,3'-dimethyl-biphenyl-4-yl)-propionitrile [ No CAS ]
  • 2
  • [ 214360-63-1 ]
  • trifluoro-methanesulfonic acid 4'-(2-cyano-ethyl)-2'-isobutyl-3,5-dimethyl-biphenyl-4-yl ester [ No CAS ]
  • 3-(2''-isobutyl-4-methoxy-3,2',6'-trimethyl-[1,1';4',1'']terphenyl-4''-yl)-propionitrile [ No CAS ]
  • 3
  • [ 214360-63-1 ]
  • trifluoro-methanesulfonic acid 2'-benzyl-4'-(2-cyano-ethyl)-3,5-dimethyl-biphenyl-4-yl ester [ No CAS ]
  • 3-(2''-benzyl-4-methoxy-3,2',6'-trimethyl-[1,1';4',1'']terphenyl-4''-yl)-propionitrile [ No CAS ]
  • 4
  • [ 214360-63-1 ]
  • 3-(2''-benzyl-4-hydroxy-3,2',6'-trimethyl-[1,1';4',1'']terphenyl-4''-yl)-propionitrile [ No CAS ]
  • 5
  • [ 214360-63-1 ]
  • 3-(2''-benzyl-4-cyanomethoxy-3,2',6'-trimethyl-[1,1';4',1'']terphenyl-4''-yl)-propionitrile [ No CAS ]
  • 6
  • [ 214360-63-1 ]
  • 3-(2''-benzyl-4-carboxymethoxy-3,2',6'-trimethyl-[1,1';4',1'']terphenyl-4''-yl)-propionic acid; compound with ammonia [ No CAS ]
  • 7
  • [ 75581-11-2 ]
  • [ 25015-63-8 ]
  • [ 214360-63-1 ]
YieldReaction ConditionsOperation in experiment
[00359] In a reaction tube under nitrogen, a mixture of PdCl2(dppf)CH2Cl2 (21 mg; 0.026 mmol) and triethylamine (0.34 ml; 2.44 mmol) in dioxane (2.5 ml; dried over 4 A sieves) was sealed and stirred at 80 C. overnight (18 h). After cooling to room temperature, HB(pin) (0.19 ml; 1.31 mmol) was added followed by 1-iodo-4-methoxy-3-methylbenzene (215 mg; 0.867 mmol) in dioxane (2.5 ml; dried over 4 A sieves) and the reaction mixture was stirred at 80 C. GC analysis after 18 hours showed a single new peak at 11.4 minutes which was identified by GC/MS as the desired arylborate compound.
  • 8
  • [ 214360-63-1 ]
  • [ 585-76-2 ]
  • [ 627906-49-4 ]
YieldReaction ConditionsOperation in experiment
68% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; dimethyl sulfoxide; at 80℃; for 12h; To a degassed (argon, 10 min) mixture of <strong>[214360-63-1]2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborolane</strong> (500 mg, 2.01 mmol), 3-bromobenzoic acid (446 mg, 2.22 mmol), and aqueous 1 M Na2CO3 solution (6.3 mL) in DMSO (20 mL) was added PdCl2dppf (1:1 complex with CH2Cl2, 132 mg, 0.16 mmol). The reaction mixture was heated to 80 C. for 12 h. The cooled mixture was acidified with aqueous 1 N HCl solution and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude resulting acid was dissolved in Et2O (150 mL) and was treated with excess ethereal CH2N2 solution (ca. 0.6 M). The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 20:1) to give the title compound (350 mg, 68% yield).
  • 9
  • [ 14804-31-0 ]
  • [ 73183-34-3 ]
  • [ 214360-63-1 ]
YieldReaction ConditionsOperation in experiment
54% A mixture of bis(pinacolato)diborane (10.7 g, 42.1 mmol), 4-bromo-1-methoxy-2-methylbenzene (7.70 g, 38.3 mmol) and KOAc (10.9 g, 114 mmol) in DMSO (200 mL) was degassed with argon for 10 min. PdCl2dppf (1:1 complex with CH2Cl2, 2.50 g, 3.06 mmol) was next added and the reaction mixture was heated to 80 C. for 24 h. The reaction mixture was diluted with water and extracted with C6H6 (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 95:5) to yield the title compound (5.1 g, 54% yield) as a colorless oil.
  • 10
  • [ 214360-63-1 ]
  • [ 1276544-73-0 ]
  • [ 1276544-74-1 ]
YieldReaction ConditionsOperation in experiment
With cesiumhydroxide monohydrate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 160℃; for 0.333333h;Inert atmosphere; CEM Discover microwave reactor; [000229] 5 ,7-Dichloro-3 -(2-chloro-4-fluorobenzyl)- 1 -(4-methoxybenzyl)- 1 H- benzo[e][l,4]diazepin-2(3H)-one (0.3 g, 0.61 mmol) was combined with lithium chloride (0.078 g, 1.83 mmol), cesium hydroxide hydrate (0.31 g, 1.83 mmol) and 2-(4-methoxy-3- methylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.151 g, 0.61 mmol) in 1,4-dioxane (3 mL) and water (0.3 mL) and the mixture was purged with nitrogen.[Tetrakis(triphenylphosphine)]palladium(0) (0.07 g, 0.061 mmol) was added and the mixture was heated in a CEM Discover microwave reactor at 160 C for 20 minutes. The mixture was allowed to cool and diluted with ethyl acetate then washed with water then brine. The organic layer was concentrated onto silica gel and chromatographed on a silica gel column eluting with 10-35% ethyl acetate in hexanes to give 7-chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-methoxy-3- methylphenyl)- 1 -(4-methoxybenzyl)- 1 H-benzo [e] [ 1 ,4]diazepin-2(3H)-one .
YieldReaction ConditionsOperation in experiment
97% General procedure: EXAMPLE 3Preparation of Aryl and Alkyl-Pinacolboranate Esters Under Barbier-Type Conditions[0075] The following procedure for the preparation m-tolyl pinacolborane isrepresentative. A 25-mL round-bottom flask equipped with a magnetic stir bar was charged with magnesium turnings (0.058 g, 2.4 mmol) and was activated by addition of iodine crystals and warming until iodine sublimed. The flask was cooled to 25 C and was purged with Ar. THF (3.5 mL) was added to the flask, followed by the addition of neatpinacolborane (0.29 mL, 2.0 mmol). m-Tolyl bromide (0.243 mL, 2.0 mmol) was then added drop wise over five minutes with constant stirring at 25 C. The reaction was complete after 3 h as evidenced by the disappearance of pinacolborane starting material ( +27.7, d, J=173.9 Hz), and the appearance of a singlet at +30.6 ppm via nB-NMR. The reaction was then cooled to 0C (ice bath) and acidified with 3 M aqueous HC1 (3 mL) (CAUTION: hydrogen evolution). After 10 min of stirring the reaction mixture was warmed to 25 C and stirred for an additional 30 min. Table entries 4, 6, 7, 8 were quenched with aqueous NH C1 (2.5 mL, 0.16 M). The reaction mixture was then transferred to a separatory funnel and extracted with diethyl ether (3 x 15 mL). The combined organic layers were dried over anhydrous MgS04, filtered, and dried under vacuo (25C, 1 Torr) to afford m-tolyl pinacolborane as a pale yellow oil. The results for the other pinacolborane esters prepared by this method are summarized in Table 2.
  • 13
  • [ 76-09-5 ]
  • 3-methyl-4-methoxyphenyl-N,N-diisopropylaminoborane [ No CAS ]
  • [ 214360-63-1 ]
YieldReaction ConditionsOperation in experiment
189 mg In a reaction flask charged with Pd(OAc)2 (4.5 mg, 0.02 mmol), potassium iodide (83 mg, 0.5 mmol), and XPhos (28 mg, 0;06 mmol) under argon atmosphere was added, in this following order: anhydrous solvent (2 mL), Et3N (0.4 mL, 3 mmol), 4-chloro-l-methoxy- 2-methylbenzene (0.16 mL, 1 mmol) and diisopropylaminoborane (0.3 mL, 2 mmol). The reaction was then heated at 50 C. After total consumption of either starting material, the reaction was cooled at -5 C, quenched with anhydrous MeOH (2 mL) and stirred for 1 h at room temperature. All volatiles were removed under vacuum before adding pinacol (153 mg, 1.3 mmol) in Et20 (2 mL), and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with Et20 (10 mL), and the organic phase was washed first with a solution of HC1 (0.1 N, 2x10 mL), followed by an aqueous solution of CuCl2 (50g/L, 3x10 mL), dried over anhydrous Na2S04, filtered and concentrated under vacuum. The crude oil was passed through a pad of silica gel, eluting with Et20. The resulting filtrate was concentrated under vacuum to afford 2-(4-methoxy- 3-methylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (189 mg, 76%). 1H NMR (300 MHz, CDCls) delta 7.69 (d, 1H, J 8.1 Hz), 7.64 (s, IH), 6.87 (d, 1H, J 8.1 Hz), 3.89 (s, 3H), 2.26 (s, 3H), 1.38 (s, 12H); 13C NMR (100 MHz, CDC13) delta 160.44, 137.15, 134.29, 125.90, 109.26, 83.50, 55.18, 24.87, 15.99; nB NMR (96 MHz, CDC13) delta +31.03; MS (EI) tR= 9.448 min; m/z: 248 (M+, 100%).
189 mg at 20℃; for 4h;Inert atmosphere; In a reaction flask charged with Pd(OAc)2 (4.5 mg, 0.02 mmol), potassium iodide (83 mg, 0.5 mmol), and XPhos (28 mg, 0;06 mmol) under argon atmosphere was added, in this following order: anhydrous solvent (2 mL), Et3N (0.4 mL, 3 mmol), 4-chloro-1-methoxy-2-methylbenzene (0.16 mL, 1 mmol) and diisopropylaminoborane (0.3 mL, 2 mmol). The reaction was then heated at 50 C. After total consumption of either starting material, the reaction was cooled at -5 C, quenched with anhydrous MeOH (2 mL) and stirred for 1 h at room temperature. All volatiles were removed under vacuum before adding pinacol (153 mg, 1.3 mmol) in Et2O (2 mL), and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with Et2O (10 mL), and the organic phase was washed first with a solution of HCl (0.1 N, 2x10 mL), followed by an aqueous solution of CuCl2 (50g/L, 3x10 mL), dried over anhydrous Na2SO4 filtered and concentrated under vacuum. The crude oil was passed through a pad of silica gel, eluting with Et2O. The resulting filtrate was concentrated under vacuum to afford 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (189 mg, 76%). 1H NMR (300 MHz, CDCl3) delta 7.69 (d, 1H, J 8.1 Hz), 7.64 (s, 1H), 6.87 (d, 1H, J 8.1 Hz), 3.89 (s, 3H), 2.26 (s, 3H), 1.38 (s, 12H); 13C NMR (100 MHz, CDCl3) delta 160.44, 137.15, 134.29, 125.90, 109.26, 83.50, 55.18, 24.87, 15.99; 11B NMR (96 MHz, CDCl3) delta +31.03; MS (EI) tR = 9.448 min; m/z: 248 (M+, 100%).
  • 14
  • [ 578-58-5 ]
  • [ 73183-34-3 ]
  • [ 214360-63-1 ]
  • [ 1417036-28-2 ]
  • 15
  • [ 214360-63-1 ]
  • N-(5-bromo-6-(phenylamino)pyridin-2-yl)pivalamide [ No CAS ]
  • N-(5-(4-methoxy-3-methylphenyl)-6-(phenylamino)pyridin-2-yl)pivalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In vaseline; N,N-dimethyl-formamide at 85℃; for 3h; Inert atmosphere;
  • 16
  • [ 214360-63-1 ]
  • N-(5-bromo-6-((4-methoxy-3-methylphenyl)amino)pyridin-2-yl)pivalamide [ No CAS ]
  • N-(5-(4-methoxy-3-methylphenyl)-6-((4-methoxy-3-methylphenyl)amino)pyridin-2-yl)pivalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In vaseline; N,N-dimethyl-formamide at 85℃; for 3h; Inert atmosphere;
  • 17
  • [ 214360-63-1 ]
  • N-(5-bromo-6-((4-isopropoxyphenyl)amino)pyridin-2-yl)-pivalamide [ No CAS ]
  • N-(6-((4-isopropoxyphenyl)amino)-5-(4-methoxy-3-methylphenyl)pyridin-2-yl)pivalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
18.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In vaseline; N,N-dimethyl-formamide at 85℃; for 3h; Inert atmosphere;
  • 18
  • [ 214360-63-1 ]
  • [ 89284-11-7 ]
  • 5-bromo-6-(4-methoxy-3-methylphenyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.7% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene at 85℃; for 4h; Inert atmosphere;
  • 19
  • [ 214360-63-1 ]
  • [ 1308677-09-9 ]
  • 5-(4-methoxy-3-methylphenyl)-6-phenylpyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.1% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 85℃; for 8h; Inert atmosphere;
  • 20
  • [ 214360-63-1 ]
  • 5-bromo-6-(4-isopropoxyphenyl)pyridin-2-amine [ No CAS ]
  • 6-(4-isopropoxyphenyl)-5-(4-methoxy-3-methylphenyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.2% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 85℃; for 8h; Inert atmosphere;
  • 21
  • [ 214360-63-1 ]
  • 5-bromo-6-(4-methoxy-3-methylphenyl)pyridin-2-amine [ No CAS ]
  • 5,6-bis(4-methoxy-3-methylphenyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 85℃; for 8h; Inert atmosphere;
  • 22
  • [ 214360-63-1 ]
  • 5-bromo-6-chloropyridin-2-ylamine [ No CAS ]
  • 6-chloro-5-(4-methoxy-3-methylphenyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.2% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 8h; Inert atmosphere;
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