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[ CAS No. 191162-40-0 ] {[proInfo.proName]}

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Chemical Structure| 191162-40-0
Chemical Structure| 191162-40-0
Structure of 191162-40-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 191162-40-0 ]

CAS No. :191162-40-0 MDL No. :MFCD01114668
Formula : C9H10BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CBPBJUTWVXLSER-UHFFFAOYSA-N
M.W : 174.99 Pubchem ID :22733820
Synonyms :

Calculated chemistry of [ 191162-40-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.03
TPSA : 45.39 Ų

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) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.94
Log Po/w (WLOGP) : -0.14
Log Po/w (MLOGP) : 0.08
Log Po/w (SILICOS-IT) : -0.69
Consensus Log Po/w : 0.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.9 mg/ml ; 0.0109 mol/l
Class : Very soluble
Log S (Ali) : -1.48
Solubility : 5.8 mg/ml ; 0.0331 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.73
Solubility : 3.24 mg/ml ; 0.0185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 191162-40-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 191162-40-0 ]

* 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 [ 191162-40-0 ]

[ 191162-40-0 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 161417-12-5 ]
  • [ 191162-40-0 ]
  • 5-(1-methyl-2-indolyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine [ No CAS ]
  • 2
  • [ 603-76-9 ]
  • [ 121-43-7 ]
  • [ 191162-40-0 ]
YieldReaction ConditionsOperation in experiment
With sec.-butyllithium; In tetrahydrofuran; 36a. 1-methylindol-2-boronic acid 1-Methylindole (0.38 mL, 3 mmol) was dissolved in THF (10 mL), and the solution was cooled to -78 C. To this solution was added sec-butyllithium (1.9 mL, 2.5 mmol), and the reaction mixture was stirred for 20 minutes. Trimethyl borate (0.34 mnL, 3 mmol) was added at -78 C., and the mixture was stirred and allowed to warm to room temperature. The reaction was quenched with water, and the solvents were removed under vacuum. The residue was taken directly to the next step.
With sec.-butyllithium; In tetrahydrofuran; 36a. 1-methylindol-2-boronic acid 1-Methylindole (0.38 mL, 3 mmol) was dissolved in THF (10 mL), and the solution was cooled to -78 C. To this solution was added sec-butyllithium (1.9 mL, 2.5 mmol), and the reaction mixture was stirred for 20 minutes. Trimethyl borate (0.34 mL, 3 mmol) was added at -78 C., and the mixture was stirred and allowed to warm to room temperature. The reaction was quenched with water, and the solvents were removed under vacuum. The residue was taken directly to the next step.
With sec.-butyllithium; In tetrahydrofuran; 36a. 1-Methylindol-2-boronic Acid 1-Methylindole (0.38 mL, 3 mmol) was dissolved in THF (10 mL), and the solution was cooled to -78 C. To this solution was added sec-butyllithium (1.9 mL, 2.5 mmol), and the reaction mixture was stirred for 20 minutes. Trimethyl borate (0.34 mL, 3 mmol) was added at -78 C., and the mixture was stirred and allowed to warm to room temperature. The reaction was quenched with water, and the solvents were removed under vacuum. The residue was taken directly to the next step.
  • 3
  • ethyl 1-(4-bromophenyl)-3-[[(trans-4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-1H-pyrazole-4-carboxylate [ No CAS ]
  • [ 191162-40-0 ]
  • ethyl 3-[[(trans-4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-1-[4-(1-methyl-1H-indol-2-yl)phenyl]-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cesium fluoride;palladium diacetate; DavePhos; In 1,4-dioxane; at 20 - 100℃; for 26h; Intermediate 53Ethyl 3-[[(frans-4-methylcyclohexyl)carbonyl](1 -methylethyl)amino]-1 -[4-(1 -methyl-1 H- indol-2-yl)phenyl]-1 H-pyrazole-4-carboxylateIntermediate 5 (200 mg), (1 -methyl-1 H-indol-2-yl)boronic acid (110 mg) cesium fluoride (191 mg) palladium (II) acetate (18.8 mg) and 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)- biphenyl (50 mg) were dissolved in dioxane (4 mL) and stirred at room temperature for 24 h. The reaction was then heated at 100C for 2 h. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with sodium bicarbonate solution brine, dried (Na2SO4) and concentrated. This residue was purified by ISCO companion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane to give the title compound. MS calcd for (C32H38N4O3 + H)+: 527 MS found (electrospray): (M+H)+ = 527
  • 4
  • [ 953780-66-0 ]
  • [ 191162-40-0 ]
  • [ 1146395-47-2 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; 1-hydroxy-7-aza-benzotriazole;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 150℃; for 0.5h;microwave irradiation; To a mixture of (1 -methyl- lH-indol-2-yl)boronic acid (37.7 mg mg, 0.215 mmol),2-(4-iodophenyl)-N- {( 1 R)- 1 -[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethyl } acetamide (50.0 mg, 0.108 mmol), tricyclohexylphosphine (0.7 mg, 0.003 mmol), l-hydroxy-7-azabenzotriazole (101 mg, 0.744 mmol) and Pd2(dba)3 (1 mg, 0.001 mmol) were added dioxane (0.4 mL) and a solution of K3PO4 in eta2O (0.2 mL, 1.27 M). The resulting solution was heated in microwave at 150 0C for 0.5 hr. The reaction was completed and diluted with EtOAc. The water later was removed. The remaining organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by reverse-phase HPLC to give the product as a TFA salt (40 mg, 79%). 1H NMR (CDCl3, 400 MHz) delta 8.22 (dd, J= 0.8, 2.8 Hz, IH), 7.63 (d, J= 8.0 Hz, IH), 7.49 (dd, J= 2.0, 6.4 Hz, 2H), 7.38 (d, J= 8.0 Hz, 2H), 7.37 (d, J= 6.4, IH), 7.27-7.19 (m, 2H), 7.14 (t, J= 8.0 Hz, IH), 6.80 (d, J= 7.2 Hz, IH), 6.56 (s, IH), 5.14 (quintet, J= 7.2 Hz, IH), 4.38 (q, J= 8.0 Hz, 2H), 3.75 (s, 3H), 3.65 (s, 2H), 1.44 (d, J= 6.8 Hz, 3H); HRMS (ES) [M+l]+ calcd for C26H25F3N3O2: 468.1893, Found: 468.1889. FLIPR alphall IP = 36 nM.
  • 5
  • [ 603-76-9 ]
  • [ 5419-55-6 ]
  • [ 191162-40-0 ]
YieldReaction ConditionsOperation in experiment
54% 1-Methylindole (200 mg, 1.52 mmol) was dissolved in THF (5 mL), and the solution was added with tert-butyllithium-pentane solution (1.48 mol/L, 1.23 mL, 1.82 mmol) by drops at -78 C for 5 minutes under argon atmosphere. The mixture was warmed to room temperature, followed by stirring for 30 minutes. The mixture was cooled to -78 C again, added with triisopropyl borate (0. 526 mL, 2.28 mmol) and warmed from -78 C to room temperature for 1 hour. The reaction mixture was added with saturated aqueous ammonium chloride solution (5 mL) and 10% aqueous potassium hydrogensulfate solution (5 mL) to adjust the pH to 2, followed by stirring at room temperature for 30 minutes. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was suspended in diisopropyl ether, then the solid was collected by filtration, washed with diisopropyl ether and then dried under reduced pressure to obtain Compound BK (144 mg, yield 54%). ESI-MS m/z: 174 [M-H]-; 1H-NMR (CDCl3)delta(ppm): 4.01 (s, 3H), 4.73 (br s, 2H), 6.97 (d, J = 0.7 Hz, 1H), 7.17 (m, 1H), 7.27-7.42 (m, 3H).
  • 6
  • [ 13535-01-8 ]
  • [ 191162-40-0 ]
  • [ 1202550-08-0 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 85℃; for 3h; A flask is charged with 3-amino-5-bromopyridine (0.173 g, 0.950 mmol), Lambda/-methyl-indole boronic acid (0.262 g, 1.425 mmol), s-Phos (0.030 g, 0.071 mmol), finely crushed potassium phosphate (0.407 g, 1.900 mmol) and toluene (4 ml_). After degassing for 30 min, Pd2dba3 (0.018 g, 0.019 mmol) is added, the flask is flushed with nitrogen and the mixture is heated to 85 0C. After 3 h, the mixture is allowed to cool to r.t., diluted with ethyl acetate and filtered through a plug of silica gel (elution with ethyl acetate). The <n="133"/>residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 3:7 to 0:1 ) to give 2-(5-amino-pyridin-3-yl)-1-methyl-1 H-indole as an off-white powder. 1H NMR (400 MHz, DMSO-cfe) delta ppm 3.74 (s, 3 H), 5.49 (s, 2 H), 6.56 (s, 1 H), 7.05 - 7.09 (m, 1 H), 7.09 - 7.10 (m, 1 H), 7.17 - 7.21 (m, 1 H), 7.49 (d, J=7.6 Hz, 1 H), 7.57 (d, J=7.6 Hz, 1 H), 7.94 (d, J=2.0 Hz, 1 H), 7.99 (d, J=2.5 Hz, 1 H). MS (ESI) m/z 224 (M+H)+.
  • 7
  • [ 146679-66-5 ]
  • [ 191162-40-0 ]
  • [ 1202550-18-2 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 120℃; for 1h;Inert atmosphere; Microwave irradiation; A microwave reactor is charged with 1-methyl-indole-2-boronic acid (1.18 g, 6.78 mmol), <strong>[146679-66-5](3-bromo-pyridin-4-yl)-methanol</strong> (0.850 g, 4.52 mmol), potassium phosphate (1.91 g, 9.04 mmol) and DMF (10 ml_). The reactor is evacuated and filled with nitrogen thrice and Pd(PPh3)4 (0.261 g, 0.226 mmol) is added. The reactor is evacuated and filled with nitrogen thrice again. The mixture is heated to 120 C for 1 h under microwave irradiation, then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo to give a residue which is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1 ) to afford [3- (1-methyl-1 H-indol-2-yl)-pyridin-4-yl]-methanol as a white solid. 1H NMR (400 MHz, MeOD) delta ppm 3.58 (s, 3 H), 4.57 (s, 2 H), 6.54 (s, 1 H), 7.14 (t, J=7.5 Hz, 1 H), 7.27 (ddd, J=7.6, 1.1 Hz, 1 H), 7.46 (d, J=8.3 Hz, 1 H), 7.62 (d, J=7.8 Hz, 1 H), 7.81 (d, J=5.1 Hz, 1 H), 8.49 (s, 1 H), 8.67 (d, J=5.1 Hz, 1 H). HRMS (ESI) m/z 239.1177 [(M+H)+ Calcd for C15H15N2O: 239.1184].
  • 8
  • [ 4408-64-4 ]
  • [ 191162-40-0 ]
  • [ 1219720-20-3 ]
YieldReaction ConditionsOperation in experiment
93% In dimethyl sulfoxide; benzene; for 3h;Inert atmosphere; Reflux; To form protected organoboronic acid 2j, the general procedure was followed using <strong>[191162-40-0]N-methylindole-2-boronic acid</strong> (3.00 g, 17.1 mmol), N-methyliminodiacetic acid (2.77 g, 18.9 mmol), benzene (60 mL) and DMSO (30 mL). The mixture was refluxed for 3 h. The product was eluted with Et2theta:MeCN 2:1 to afford the boronate ester 2j as a colorless crystalline solid (4.55 g, 93%). TLC (EtOAc) Rf = 0.39, visualized by UV (254 nm) and KMnO4. 1H-NMR (500 MHz, CD3CN) delta 7.57 (app dt, / = 8.0, 1.0 Hz, 1 H), 7.39 (dd, / = 8.0, 1.0 Hz, 1 H), 7.20 (ddd, / = 8.0, 7.0, 1.0 Hz, 1 H), 7.04 (ddd, / = 8.0, 7.0, 1.0 Hz, 1 H), 6.66 (d, / = 1.0 Hz, 1 H), 4.07 (d, / = 1 7 Hz, 2H), 3.92 (d, / = 1 7 Hz, 2H), 3.82 (s, 3H), 2.56 (s, 3H). 13C-NMR (125 MHz, CD3CN) delta 169.4, 141.3, 129.0, 122.9, 121.5, 120.0, 1 1 1.4, 1 10.6, 62.3, 47.8, 32.8. 11 B-NMR (96 MHz, CD3CN) delta 10.8. HRMS (EI +) Calculated for C14H15BN2O4 (M) + : 286.1 125, Found: 286.1 127. IR (thin film, cm -1) 3000, 2948, 1765, 1653, 1617, 1508, 1456, 1509, 1456, 1360, 1332, 1276, 1236, 1 161 , 1037, 998, 962, 897, 859.
  • 9
  • [ 464192-28-7 ]
  • [ 191162-40-0 ]
  • [ 1248681-42-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 20℃;Inert atmosphere; Production Example 1; 2-( 1 -Methyl- lH-indol-2-yl)- 1 ,3-thiazole-5-carbaldehyde; A dimethoxyethane solution (15 mL) of commercially available ( 1 -methyl- lH-indol- 2-yl)boronic acid (328 mg), commercially available 2-bromo-l,3-thiazole-5-carbaldehyde (300 mg), tetrakis(triphenylphosphine)palladium(0) (181 mg), and 1 M sodium carbonate aqueous solution (4.7 mL) was stirred overnight at room temperature in a nitrogen atmosphere. The dimethoxyethane was distilled off under reduced pressure, and the resulting residue was extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 3:2) to give the title compound (160 mg) as a pale yellow solid.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 20℃;Inert atmosphere; A dimethoxyethane solution (15 mL) of commercially available (1-methyl-1H-indol-2-yl)boronic acid (328 mg), commercially available <strong>[464192-28-7]2-bromo-1,3-thiazole-5-carbaldehyde</strong> (300 mg), tetrakis(triphenylphosphine)palladium(0) (181 mg), and 1 M sodium carbonate aqueous solution (4.7 mL) was stirred overnight at room temperature in a nitrogen atmosphere. The dimethoxyethane was distilled off under reduced pressure, and the resulting residue was extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give the title compound (160 mg) as a pale yellow solid.
  • 10
  • [ 1248681-43-7 ]
  • [ 191162-40-0 ]
  • [ 1248681-26-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃;Inert atmosphere; Example 2; 2- { 5-Fluoro-4-[(4-methylpiperazin- 1 -yl)methyl]pyridin-2-yl} - 1 -methyl- 1 H-indole fumarate; The compound (850 mg) obtained in Production Example 2, commercially available (1 -methyl- lH-indol-2-yl)boronic acid (671 mg), and tetrakistriphenylphosphine palladium (403 mg) were added to a mixed solution of toluene (30 mL)-ethanol (15 mL)-2 M sodium carbonate aqueous solution (7 mL). After flushing the reaction system with argon gas, the mixture was stirred at 1000C over night. After cooling, the reaction mixture was extracted with ethyl acetate. The organic layer was then washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: methanol = 100:1 to 70:1) to obtain a free form of the title compound (284 mg) as a yellow oily liquid. At room temperature, an ethanol solution (8 mL) of fumaric acid (97 mg) was gradually added to a stirred ethyl acetate solution (40 mL) of the oily liquid obtained as above. After 1-hour stirring at room temperature, the precipitate was filtered off, and thoroughly washed with ethyl acetate. The resulting solid was dried under reduced pressure to give the title compound (250 mg) as a white solid. 1Eta-NMR (400 MHz, DMSO-d6, deltappm): 2.26 (3H, s), 2.40-2.60 (8H, m), 3.67 (2H, s), 4.00 (3H, s), 6.59 (2H, s), 6.92 (IH, s), 7.07-7.11 (IH, m), 7.21-7.25 (IH, m), 7.52 (IH, d, J = 8.0 Hz), 7.61 (IH, d, J = 8.0 Hz), 7.90 (IH, d, J = 6.0 Hz), 8.64 (IH, s). ESI-MS Found: m/z 339[M+H]+
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃;Inert atmosphere; A dimethoxyethane solution (15 mL) of commercially available <strong>[191162-40-0](1-methyl-1H-indol-2-yl)boronic acid</strong> (328 mg), commercially available 2-bromo-1,3-thiazole-5-carbaldehyde (300 mg), tetrakis(triphenylphosphine)palladium(0) (181 mg), and 1 M sodium carbonate aqueous solution (4.7 mL) was stirred overnight at room temperature in a nitrogen atmosphere. The dimethoxyethane was distilled off under reduced pressure, and the resulting residue was extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give the title compound (160 mg) as a pale yellow solid.
  • 11
  • [ 1039826-64-6 ]
  • [ 191162-40-0 ]
  • [ 1108184-46-8 ]
  • 12
  • [ 191162-40-0 ]
  • [ 1202551-38-9 ]
  • 13
  • [ 191162-40-0 ]
  • [ 1202552-33-7 ]
  • 14
  • [ 191162-40-0 ]
  • 2-methyl-1-(1-[5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylamino]-methyl}-cyclobutyl)-propan-1-one [ No CAS ]
  • 15
  • [ 191162-40-0 ]
  • [ 1248681-25-5 ]
  • 16
  • [ 162102-79-6 ]
  • [ 191162-40-0 ]
  • [ 1355594-81-8 ]
YieldReaction ConditionsOperation in experiment
59% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In methanol; water; toluene; at 70℃; for 19h;Inert atmosphere; A mixture of <strong>[162102-79-6]4-bromopyridine-2,6-dicarboxylic acid dimethyl ester</strong> (548 mg, 2.00 mmol), 1-methylindole-2-boronic acid (402 mg, 2.30 mmol), sodium bicarbonate (342 mg, 4.07 mmol), and tetrakis(triphenylphosphine)palladium (68 mg, 0.08 mmol) was placed in a 100 mL-flask and dried under vacuum for 2.5 h. In a separate flask, a mixture of toluene (30 mL), methanol (7.5 mL) and water (7.5 mL) was degassed by bubbling argon gas for 2.5 h. The degassed solvent mixture was added to the dried reagents and the combined ingredients were stirred under argon atmosphere at 70 C. After stirring for 19 h, the mixture was cooled to room temperature, diluted with dichloromethane, washed with brine and dried over sodium sulfate. After rotary evaporation, the residue was purified using silica gel chromatography (40% ethyl acetate in hexanes) to provide 5 (420 mg, 59% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.47 (s, 2H), 7.69 (td, J = 1.00, 7.60 Hz, 1H), 7.42 (dd, J = 0.80, 8.40 Hz, 1H), 7.35 (dt, J = 1.20, 8.40 Hz, 1H), 7.20 (ddd, J = 1.20, 7.20, 8.00 Hz, 1H), 6.91 (d, J = 0.80 Hz, 1H), 4.07 (s, 6H), 3.88 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 165.26, 148.76, 143.28, 139.89, 136.60, 127.66, 127.00, 123.88, 121.62, 120.86, 110.23, 105.73, 53.54, 31.97.
  • 17
  • [ 191162-40-0 ]
  • [ 1355594-82-9 ]
  • 18
  • [ 191162-40-0 ]
  • [ 1355594-85-2 ]
  • 19
  • [ 405939-39-1 ]
  • [ 191162-40-0 ]
  • [ 1361380-55-3 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 150℃; for 0.5h;Inert atmosphere; Microwave irradiation; Example 22Preparation of (2-chlorophenyl)-N-[5-(1-methylindol-2-yl)(1,3-thiazol-2-yl)]carboxamide (54): Preparation of 5-(1-methylindol-2-yl)-1,3-thiazole-2-ylamine (53): A mixture of (tert-butoxy)-N-(5-bromo(1,3-thiazol-2-yl)carboxamide (52, 140 mg, 0.5 mmol), 1-methylindol-2-yl boronic acid (88 mg, 0.5 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex (1:1) (40 mg) and potassium phosphate (106 mg) in 2 ml DMF and 0.5 ml water was heated under Ar in microwave reactor at 150 C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to silica gel flash column purification (0-100% B, A: hexane; B: EA) to give 21 mg 5-(1-methylindol-2-yl)-1,3-thiazole-2-ylamine (53) as brown solid (yield: 18.3%; purity>90%).
  • 20
  • [ 191162-40-0 ]
  • [ 1361379-27-2 ]
  • 21
  • [ 258506-66-0 ]
  • [ 191162-40-0 ]
  • [ 1373271-29-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110℃; for 1h;Microwave irradiation; INTERMEDIATE 50 2-(6-Chloropyridin-2-yl)-l-methyl-lH-indole 2-Chloro-6-iodopyridine (400 mg, 1.67 mmol), N-methylindole-2-boronic acid (292 mg, 1.67 mmol), tetrakis(triphenylphosphine)palladium (0) (154 mg, 0.13 mmol) and Na2C03 (442 mg, 4.18 mmol) were dissolved in water (10 mL) and dioxane (10 mL) and heated using a microwave (110 C, absorption high) for 1 h. The solvents were removed in vacuo and the residue was partitioned between DCM (50 mL) and water (30 mL). The aq fraction was extracted with DCM (30 mL) and the combined organic fractions were dried (MgSC^) and concentrated in vacuo to give the crude title compound (406 mg) as a brown gum. LCMS (ES+): 243.2 [MH]+.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 110℃; for 1h;Microwave irradiation; 2-Chloro-6-iodopyridine (400 mg, 1.67 mmol), N-methylindole-2-boronic acid (292 mg, 1.67 mmol), tetrakis(triphenylphosphine)palladium (0) (154 mg, 0.13 mmol) and Na2CO3 (442 mg, 4.18 mmol) were dissolved in water (10 mL) and dioxane (10 mL) and heated using a microwave (110 C., absorption high) for 1 h. The solvents were removed in vacuo and the residue was partitioned between DCM (50 mL) and water (30 mL). The aq fraction was extracted with DCM (30 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound (406 mg) as a brown gum. LCMS (ES+): 243.2 [MH]+.
  • 22
  • [ 191162-40-0 ]
  • ethanesulfonic acid [5-(1-methyl-1H-indol-2-yl)pyridin-3-yl]-N-ethanesulfonyl amide [ No CAS ]
  • 23
  • [ 191162-40-0 ]
  • C19H20N4O4S2 [ No CAS ]
  • 24
  • [ 191162-40-0 ]
  • ethanesulfonic acid [5-(3-cyano-1-methyl-1H-indol-2-yl)pyridin-3-yl]amide [ No CAS ]
  • 25
  • [ 1202551-96-9 ]
  • [ 191162-40-0 ]
  • [ 1202551-97-0 ]
  • 26
  • (Z)-N’-((2-bromoallyl)oxy)-6-methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinimidamide [ No CAS ]
  • [ 191162-40-0 ]
  • (Z)-6-methoxy-5-(4-methyl-1H-imidazol-1-yl)-N’-((2-(1-methyl-1H-indol-2-yl)allyl)oxy)picolinimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 20 - 100℃; for 1h;Inert atmosphere; Under argon, a microwave vial was charged with (Z)-iV-((2- bromoallyl)oxy)-6-methoxy-5-(4-methyl- 1H-imidazol- 1 -yl)picolinimidamide (600 mg, 1.6 mmol), 1-Methyl-1H-indol-2-yl-2-boronic acid (315 mg, 1.8 mmol), sodium carbonate (521 mg, 4.9 mmol) and Pd(PPh3)4 (95 mg, 0.08 mmol). Next, degassed 1,2-dimethoxyethane (14 mL) and water (4 mL) were added and the resultant mixture was heated in an oil-bath at 100C for 1 hour. The mixture was diluted with water and extracted twice with EtOAc. The combined organic layers were washed with water, brine, dried with sodium sulfate, concentrated in vacuo and the residue was purified by silica column chromatography [5% methanol in EtOAcj to afford (Z)-6-methoxy-5-(4-methyl- 1 H-imidazol- 1 -yl)-N-((2-( 1- methyl-1H-indol-2-yl)allyl)oxy)picolinimidamide (491 mg, 85%) as a colorless oil. ?H NMR (CDC13, 400 MHz) 7.82 (d, I = 1.3 Hz, 1H), 7.68 (d, I = 8.0 Hz, 1H), 7.65 - 7.60 (m, 1H), 7.57 (d, I = 8.0 Hz, 1H), 7.37 - 7.32 (m, 1H), 7.28 - 7.22 (m, 1H), 7.16 -7.11 (m, 1H), 7.02- 6.97 (m, 1H), 6.59 (d, I = 0.7 Hz, 1H), 5.73 (d, I = 1.3 Hz, 1H), 5.55 -5.31 (m, 3H), 4.98(s, 2H), 4.07 (s, 3H), 3.81 (s, 3H), 2.32 (d, I = 0.9 Hz, 3H); LCMS: 97.7%; 417.2 (M+1); RT 2.24 mm. (method A); TLC: 5% MeOH/ EtOAc (R1 0.35).
  • 27
  • C7H9ClN4O [ No CAS ]
  • [ 191162-40-0 ]
  • 5-(1-methyl-1H-indol-2-yl)-3-morpholino-1,2,4-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50 mg With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 150℃; for 0.25h;Microwave irradiation; To a mixed solution of the compound 1 (60 mg), the compound 2 (63 mg), and dichlorobis(triphenylphosphine) palladium (10 mg) in dioxane (2 mL) was added an aqueous solution of 2 mol/L sodium carbonate (1.0 mL). The reaction mixture was stirred for 15 minutes at 150 C in a microwave reactor (Initiator, Biotage). The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and then the solution was washed with water and brine, and dried. The solvent was evaporated under reduced pressure, then the resulting crystalline residue was suspended and washed in a mixed solvent of hexane-ethyl acetate (2:1), taken by filtration, and dried to give 5-(1-methyl-1H-indol-2-yl)-3-morpholino-1,2,4-triazine (50 mg) as a yellow solid. MS (APCI) 296 [M+H]+
  • 28
  • [ 64-18-6 ]
  • (3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-bromo-5-methylpyrazin-2-yl)methanol [ No CAS ]
  • [ 191162-40-0 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-methyl-6-(1-methyl-1H-indol-2-yl)pyrazin-2-yl}methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% A vial was charged with (3-((3,S',4)S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan- 8-yl)-6-bromo-5-methylpyrazin-2-yl)methanol (96 mg, 0.259 mmol, 1 equiv), (1-methyl-lH- indol-2-yl)boronic acid (68 mg, 0.388 mmol, 1.5 equiv), tetrakis(triphenylphosphine)palladium (60 mg, 0.0519 mmol, 0.2 equiv), potassium carbonate (107 mg, 0.776 mmol, 3 equiv), and a stir bar. Degassed ethanol (1.72 mL) was added, the vial capped, and the headspace evacuated and filled with nitrogen three times. The vial was placed in an 80 C oil bath overnight. The reaction mixture was filtered through a pad of Celite and the filtrate concentrated. The crude product was purified by preparative HPLC to afford (3-((3,S',4)S)-4-amino-3-methyl-2-oxa-8- azaspiro[4.5]decan-8-yl)-5-methyl-6-(l-methyl-lH-indol-2-yl)pyrazin-2-yl)methanol (26 mg, 24%) as its formate salt. 1H MR (500 MHz, MeOH-i) delta 8.57 (s, 1H), 7.60 (m, 1H), 7.45 (m, 1H), 7.25 (m 1H), 7.11 (m 1H), 6.62 (S, 1H) 4.73 (s, 2H), 4.38 - 4.18 (m, 1H), 3.94 (d, J = 8.8 Hz, 1H), 3.82 (d, J= 8.8 Hz, 1H), 3.74 (s, 3H), 3.71 - 3.64 (m, 2H), 3.26 - 2.96 (m, 3H), 2.52 (s, 3H), 2.08 - 1.91 (m, 2H), 1.85 (d, J = 13.4 Hz, 1H), 1.76 (d, J = 12.4 Hz, 1H), 1.30 (d, J Hz, 3H). LC-MS (ESI): m/z: [M + H] calculated for C24H31N5O2: 422.3; found: 422.5.
  • 29
  • 5'-iodo-1'-methylspiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
  • [ 191162-40-0 ]
  • 1'-methyl-5'-(1-methyl-1H-indol-2-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
  • 30
  • N-(quinolin-8-yl)but‐3‐enamide [ No CAS ]
  • [ 191162-40-0 ]
  • C22H21N3O [ No CAS ]
  • 31
  • [ 191162-40-0 ]
  • 14-methyl-9-methylene-9,14-dihydrodibenzo[4,5:6,7]cyclohepta[1,2-b]indole [ No CAS ]
  • 32
  • [ 191162-40-0 ]
  • 2-(2-iodophenyl)-1-methyl-1H-indole [ No CAS ]
  • 33
  • [ 615-43-0 ]
  • [ 191162-40-0 ]
  • [ 65610-86-8 ]
  • 34
  • [ 191162-40-0 ]
  • 10-(diphenylmethylene)-5-methyl-5,10-dihydroindeno[1,2-b]indole [ No CAS ]
  • 35
  • Ac-Gly-Pro-Dha-Phe-NH<SUB>2</SUB> [ No CAS ]
  • [ 191162-40-0 ]
  • C30H36N6O5 [ No CAS ]
  • 36
  • [ 1448637-27-1 ]
  • [ 191162-40-0 ]
  • C25H28N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; water; at 73℃; for 12h;Inert atmosphere; Compound NAP 0.169g, 1-methylindole-2-boronic acid, potassium carbonate, bistriphenylphosphonium palladium dichloride, tetrahydrofuran, and water obtained in the first set of experiments in Example 1 were added to the flask in turn, and the flask was heated under an inert gas atmosphere. Atmosphere, stirring, heating and condensation reflux for 12h. After the reaction was completed, the solution was extracted with dichloromethane, the organic phase was collected, the solvent was removed under reduced pressure, and the system of petroleum ether:ethyl acetate (20:1) was used as the eluent for column chromatography to obtain the compound MIPMD. Three groups of experiments were carried out, and the ratio conditions of different materials are shown in Table 14 below.
  • 37
  • 3'-(diethylamino)-6'-iodo-3H-spiro[isobenzofuran-1,9'-xanthene]-3-one [ No CAS ]
  • [ 191162-40-0 ]
  • C33H28N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; water; at 73℃; for 12h;Inert atmosphere; Compound RHO 0.25g, 1-methylindole-2-boronic acid, potassium carbonate, bistriphenylphosphonium palladium dichloride, tetrahydrofuran, and water obtained in the first group of experiments in Example 7 were added to the flask in turn, and the flask was heated under an inert gas atmosphere. Atmosphere, stirring, heating and condensation reflux for 12h. After the reaction, the solution was extracted with dichloromethane, the organic phase was collected, the solvent was removed under reduced pressure, and the system of petroleum ether:ethyl acetate (4:1) was used as the eluent for column chromatography to obtain the compound MIRHO. Three groups of experiments were carried out, and the ratio conditions of different materials are shown in Table 16 below.
  • 38
  • [ 1193092-32-8 ]
  • [ 191162-40-0 ]
  • C29H30N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; at 73℃; for 12h;Inert atmosphere; Compound NAP 0.194g, 1-methylindole-2-boronic acid, potassium carbonate, bistriphenylphosphonium palladium dichloride, tetrahydrofuran, and water obtained in the first set of experiments in Example 1 were added to the flask in turn, and the flask was heated under an inert gas atmosphere. Atmosphere, stirring, heating and condensation reflux for 12h. After the reaction was completed, the solution was extracted with dichloromethane, the organic phase was collected, the solvent was removed under reduced pressure, and the compound MINAP was obtained by column chromatography using petroleum ether:ethyl acetate (15:1) system as the eluent. Three groups of experiments were carried out, and the ratio conditions of different materials were shown in Table 3 below.
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