天堂网亚洲,天天操天天搞,91视频高清,菠萝蜜视频在线观看入口,美女视频性感美女视频,95丝袜美女视频国产,超高清美女视频图片

Home Cart 0 Sign in  

[ CAS No. 376584-63-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 376584-63-3
Chemical Structure| 376584-63-3
Structure of 376584-63-3 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 376584-63-3 ]

Related Doc. of [ 376584-63-3 ]

Alternatived Products of [ 376584-63-3 ]
Product Citations

Product Details of [ 376584-63-3 ]

CAS No. :376584-63-3 MDL No. :MFCD02020768
Formula : C3H5BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NEUWPDLMDVINSN-UHFFFAOYSA-N
M.W : 111.90 Pubchem ID :11251979
Synonyms :

Calculated chemistry of [ 376584-63-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 28.41
TPSA : 69.14 ?2

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) : -7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.84
Log Po/w (WLOGP) : -1.91
Log Po/w (MLOGP) : -2.25
Log Po/w (SILICOS-IT) : -1.27
Consensus Log Po/w : -1.25

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.4
Solubility : 44.4 mg/ml ; 0.397 mol/l
Class : Very soluble
Log S (Ali) : -0.13
Solubility : 82.7 mg/ml ; 0.739 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.07
Solubility : 96.1 mg/ml ; 0.859 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 376584-63-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 376584-63-3 ]

* 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.

  • Downstream synthetic route of [ 376584-63-3 ]

[ 376584-63-3 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 162356-90-3 ]
  • [ 376584-63-3 ]
  • [ 449758-18-3 ]
  • 2
  • [ 449758-17-2 ]
  • [ 376584-63-3 ]
YieldReaction ConditionsOperation in experiment
48% With n-butyllithium; triisopropylborane; In tetrahydrofuran; hexane; at -78 - 20℃; for 5h; To a cooled solution (-780C) of l-(tetrahydro-pyran-2-yl)-lH-pyrazole (7.6g,52mmol) in THF (5OmL), "BuLi (33mL, 2.5M in hexane, 82.5mmol) and triisopropyl borane (12.7mL, 55mmol) are added dropwise maintaining the temperature at -7O0C. The reaction mixture is stirred at -7O0C for one hour and then allowed to reach room temperature over 4 hours. After quenching the reaction with 2M HCl, the solvent is removed in vacuo and the pH is adjusted to pH 6 using IM NaOH. A precipitate is formed, collected by filtration and washed with toluene and petroleum ether. Trituration with ethyl acetate affords the target compound as a white solid (2.7g, 48percent), which is used in the next step without further purification.
  • 3
  • [ 108-86-1 ]
  • [ 376584-63-3 ]
  • [ 2458-26-6 ]
  • 4
  • [ 959709-11-6 ]
  • [ 376584-63-3 ]
  • [ 1009378-48-6 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 16h; Example 32 Synthesis of 4-methy--2-(2iy-pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid benzyl amide (2.0 g, 6.43 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added IH- pyrazole-5-boronic acid (1.44 g, 12.9 mmol), Pd(PPh3)4 (0.74 g, 0.643 mmol), and potassium carbonate (2.67 g, 19.3 mmol). The resulting mixture was degassed three times and heated to 100 0C for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed with brine (2 x 100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (ethyl acetate :hexane, 1 :1) to provide 4-methyl-2- (2H-pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide (1.25 g, 66percent yield) as a white solid. 1H NMR (400 MHz, DMSCW6) delta 8.76 (t, J = 4.0 Hz, IH), 7.89 (d, J = 4.0 Hz, 1 H), 7.31-7.36 (m, 4H)5 1. IA-1.21 (m, 1 H), 6.78 (d, J = 4.0 Hz, IH), 4.44 (d, J = 4.0 Hz, 2H), 2.60 (s, 3H); MS (M+H)+ = 299.1 ; R1 = 1.06 min; HRMS (M+H)+= 299.10.; Example 90 Part B. Synthesis of 4-methyl-2-(2H-pyrazoI-3-yI)-thiazole-5-carboxylic acid benzylamideA solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid benzyl amide (2.0 g, 6.43 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added 1 H-pyrazole-5- boronic acid (1.44 g, 12.86 mmol), Pd(PPh3)4 (0.74 g, 0.643 mmol), and potassium carbonate (2.67 g, 19.29 mmol). The resulting mixture was degassed three times and heated to 100 0C for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with brine (2 x 100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel eluting with 1 :1 ethyl acetate:hexane to provide 4-methyl- 2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide (1 .25 g, 66percent yield) as a white solid. MS (M+eta)+ = 299; R, = 1.06 min; HRMS (M + H) + = 299.
  • 5
  • [ 22900-83-0 ]
  • [ 376584-63-3 ]
  • 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 16h; To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (2.0 g, 7.99 mmol) in toluene (60 mL), water (20 mL) and ethanol (20 mL) was added IH- pyrazole-5-boronic acid (1.79 g, 15.99 mmol), Pd(PPh3^ (0.92 g, 0.80 mmol), and <n="82"/>50352potassium carbonate (3.30 g, 23.98 mmol). The resulting mixture was degassed three times and heated to 100 0C for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with brine (2 x 100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography (hexanes:ethyl acetate, 1 : 1) to provide 4-methyl-2-(2H-pyrazol- 3-yl)-thiazole-5-carboxylic acid ethyl ester (1.5 g, 83percent yield) as a yellow solid. MS (M+eta)+ = 238; R, = 1.2 min.
  • 6
  • [ 1009378-44-2 ]
  • [ 376584-63-3 ]
  • [ 1009378-45-3 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 16h; To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid (pyridine-3- ylmethyl)-amide (5.0 g, 16.0 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added lH-pyrazole-5-boronic acid (2.15 g, 19.2 mmol), Pd(PPh3)4 (1.85 g, 1.60 mmol), and potassium carbonate (6.64 g, 48.1 mmol). The resulting mixture was degassed three times and heated to 1000C for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with brine (2 x 100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was recrystallized from ethyl acetate to provide 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5- carboxylic acid (pyridine-3-ylmethyl)amide as a white solid (4.20 g, 85percent yield).
  • 7
  • [ 1009378-33-9 ]
  • [ 376584-63-3 ]
  • 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid 4-fluoro-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); at 100℃; for 16h; To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamide (5.0 g, 15.0 mmol) in toluene (3OmL), water (10 mL) and ethanol (10 mL) was added IH- pyrazole-5-boronic acid (1.70 g, 15.0 mmol), Pd(PPh3)4 (1.75 g, 1.52 mmol), and potassium carbonate (6.3 g, 45.6 mmol). The resulting mixture was degassed three times and heated to 100 0C for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with brine (2 x 100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography over silica gel (ethyl acetate:hexane, 50:50) to provide 4-methyl-2-(2H-pyrazol-S-yO-thiazole-S-carboxylic acid 4-fluoro-benzylamide as yellow solid (3.25 g 68 percent) MS (M+H)+= 317; R1 = 1.13 min; HRMS (M+H)+= 317.
  • 8
  • [ 919291-24-0 ]
  • [ 376584-63-3 ]
  • C19H18N4O [ No CAS ]
  • 9
  • [ 919291-43-3 ]
  • [ 376584-63-3 ]
  • 6-(2-aminoethyl)-9-(1H-pyrazol-5-yl)benzo[h]isoquinolin-1(2H)-one [ No CAS ]
  • 10
  • [ 870563-35-2 ]
  • [ 376584-63-3 ]
  • [ 870563-38-5 ]
YieldReaction ConditionsOperation in experiment
62% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); Intermediate 174, N-(4-fluoro-2-iodobenzyl)-3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide (0.150 g, 0.27 mmol) was reacted with <strong>[376584-63-3]1H-pyrazol-5-ylboronic acid</strong> (0.060 g, 0.54 mmol), sodium carbonate (0.085 g, 0.81 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.070 g) to give 0.085 g (62percent yield) of the title material as a white solid after chromatography on silica gel. 1HNMR 400 MHz (CDCl3) ? (ppm): 1.63 (6H, s, 2xCH3), 4.03 (4H, m, 2xCH2), 4.65 (2H, d, J=6.5 Hz, NCH2), 5.25 (2H, s, OCH2), 6.54 (1H, d, J=2.5 Hz, CH), 7.03 (1H, m, aromatic), 7.25 (1H, dd, J=2.5 Hz and J=9.8 Hz, aromatic), 7.35 (3H, m, aromatics), 7.53 (2H, m, aromatics), 7.56 (1H, d, J=2.5 Hz, CH), 7.60 (1H, dd, J=6.1 Hz and J=8.6 Hz, aromatic), 8.96 (1H, broad t, NH). HRMS (ESI+) calculated for C27H27FN5O4 [M+H+]: 504.2047: found: 504.2068.
  • 11
  • [ 934493-80-8 ]
  • [ 376584-63-3 ]
  • [ 934493-81-9 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 20℃; for 4h;Heating / reflux; [00207] To a solution of 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 7(8H)-one (0.765 g, 2.43 mmol) in DME-H2O (10:1 11 mL) was added lH-pyrazol-5- ylboronic acid (Frontier, 0.408 g, 3.65 mmol), [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd(dpprhof),0.198 g, 0.243 mmol) and triethylamine (0.736 g, 7.29 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 4 h. After cooling down to room temperature, the reaction mixture was partitioned with water and ethyl acetate. After separation, the organic layer was dried with Na2SO4, and the product 8-ethyl-4-methyl- 2-(methylthio)-6-(lH-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.567 g, 77percent yield) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CDCl3): delta 13.3 (bs, IH), 8.54 (s, IH), 7.82-7.07 (m, 2H), 4.45 (q, J= 7.2 Hz, 2H), 2.71 (s, 3H), 2.60 (s, 3H), 1.26 (t, J= 7.2Hz, 3H). EPO <DP n="66"/>
77% With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 20℃; for 4h;Heating / reflux; To a solution of 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 7(8H)-one (0.765 g, 2.43 mmol) in DME-H2O (10: 1 1 1 mL) was added l H-pyrazol-5-ylboronic acid (Frontier, 0.408 g, 3.65 mmol), [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd(dpppf),0.198 g, 0.243 mmol) and triethylamine (0.736 g, 7.29 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 4 h. After cooling down to room temperature, the reaction mixture was partitioned with water and ethyl acetate. After separation, the organic layer was dried with Na2SO4, and the product 8-ethyl-4-methyl-2-(methylthio)-6-(lH-pyrazol- 5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.567 g, 77percent yield) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CDCl3): delta 13.3 (bs, IH), 8.54 (s, IH), 7.82-7.07 (m, 2H), 4.45 (q, J = 7.2 Hz, 2H), 2.71 (s, 3H), 2.60 (s, 3H), 1.26 (t, J = 7.2Hz, 3H).
77% With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 20℃; for 4h;Heating / reflux; [00242] To a solution of 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 7(8H)-one (0.765 g, 2.43 mmol) in DME-H2O (10:1 11 mL) was added lH-pyrazol-5- ylboronic acid (Frontier, 0.408 g, 3.65 mmol), [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd(dpppf),0.198 g, 0.243 mmol) and triethylamine (0.736 g, 7.29 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 4 h. After cooling down to room temperature, the reaction mixture was partitioned with water and ethyl acetate. After separation, the organic layer was dried with Na2SO4, and the product 8-ethyl-4-methyl- <n="74"/>2-(methylthio)-6-(lH-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.567 g, 77percent yield) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CDCl3): delta 13.3 (bs, IH), 8.54 (s, IH), 7.82-7.07 (m, 2H), 4.45 (q, J= 7.2 Hz, 2H), 2.71 (s, 3H), 2.60 (s, 3H), 1.26 (t, J= 7.2Hz, 3H).
  • 12
  • [ 934494-01-6 ]
  • [ 376584-63-3 ]
  • [ 934494-02-7 ]
YieldReaction ConditionsOperation in experiment
13.7% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; Intermediate 6; [00234] In a 350 mL pressure tube 2-amino-6-bromo-8-isopropyl-4-methylpyrido[2,3- d]rhoyrimidin-7(8H)-one (1.50 g, 5.05 mmol), l/f-pyrazol-3-yl boronic acid (1.12 g, 10.09 mmol), K2CO3 (336 mg, 15.1 mmol), and tetrakis(triphenylphosphine) palladium (0) (583 mg, 0.0504 mmol) were dissolved in 50 mL dioxane and 5 mL H2O. The tube was sealed, heated to 100 0C and allowed to react overnight. A color change was observed. LCMS indicated no presence of starting material. Sample was filtered through a syringe filter and evaporated to dryness. Compound was dissolved in ethyl acetate and triturated in hexane. Light yellow powder of 2-ammo-8-isopropyl-4-methyl-6-(lH-pyrazol-5-yl)pyrido[2,3- EPO <DP n="76"/>d]pyrimidin-7(8H)-one (195 mg, 13.7percent yield) was found to be 98percent pure by etaPLC. 1H NMR (400MHz, CDCl3) delta 12.97 (br s, IH), 8.35 (s, IH), 7.60 (br s, IH), 7.21 (s, 2H), 6.94 (s, IH)5 5.86 (br s, IH), 2.50 (m, 6H), 1.54 (s, 3H), MS (EI) for C14H16N6O: 285.0 (MH+).
13.7% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; In a 350 mL pressure tube 2-amino-6-bromo-8-isopropyl-4-methylpyrido[2,3- d]pyrimidin-7(8H)-one (1.50 g, 5.05 mmol), leta-pyrazol-3-yl boronic acid (1.12 g, 10.09 mmol), K2CO3 (336 mg, 15.1 mmol), and tetrakis(triphenylphosphine) palladium (0) (583 mg, 0.0504 mmol) were dissolved in 50 mL dioxane and 5 mL H2O. The tube was sealed, heated to 100 0C and allowed to react overnight. A color change was observed. LCMS indicated no presence of starting material. Sample was filtered through a syringe filter and evaporated to dryness. Compound was dissolved in ethyl acetate and triturated in hexane. Light yellow powder of 2-amino-8-isopropyl-4-methyl-6-(lH-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)- one (195 mg, 13.7percent yield) was found to be 98percent pure by etaPLC. 1H NMR (400MHz, CDCl3) delta 12.97 (br s, I H), 8.35 (s, IH), 7.60 (br s, IH), 7.21 (s, 2H), 6.94 (s, IH), 5.86 (br s, IH), 2.50 (m, 6H), 1.54 (s, 3H), MS (EI) for C14H16N6O: 285.0 (MH+).
13.7% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; Synthesis 6; [00268] In a 350 mL pressure tube 2-amino-6-bromo-8-isopropyl-4-methylpyrido[2,3- d]pyrimidin-7(8H)-one (1.50 g, 5.05 mmol), lH-pyrazol-3-yl boronic acid (1.12 g, 10.09 mmol), K2CO3 (336 mg, 15.1 mmol), and tetrakis(triphenylphosphine) palladium (0) (583 mg, 0.0504 mmol) were dissolved in 50 mL dioxane and 5 mL H2O. The tube was sealed, heated to 100 0C and allowed to react overnight. A color change was observed. LCMS indicated no presence of starting material. The sample was filtered through a syringe filter and evaporated to dryness. The compound was dissolved in ethyl acetate and triturated in hexane. Light yellow powder of 2-amino-8-isopropyl-4-methyl-6-(lH-pyrazol-5- yl)pyrido[2,3-d]pyrimidin-7(8H)-one (195 mg, 13.7percent yield) was found to be 98percent pure by etaPLC. 1H NMR (400MHz, CDCl3) delta 12.97 (br s, IH), 8.35 (s, IH), 7.60 (br s, IH), 7.21 (s, 2H), 6.94 (s, 1eta), 5.86 (br s, 1eta), 2.50 (m, 6eta), 1.54 (s, 3H), MS (EI) for Ci4Hi6N6O: 285.0 (MH+).
  • 13
  • [ 942411-15-6 ]
  • [ 376584-63-3 ]
  • (RS)-N-(ethoxycarbonyl)-S-(4-[4-[(R)-2-hydroxy-1-methylethyl]amino}-5-(5-pyrazol)pyrimindin-2-yl]amino}phenyl)-S-methylsulfoximide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 0.25h;Microwave irradiation; Example 4.4; (RS)-N-(ethoxycarbonyl)-S-(4-[4-[(R)-2-(hydroxy-1-methylethyl]amino}-5-(5- pyrazol)pyrimindin-2-yl]amino}phenyl)-S-methylsulfoximide; <n="226"/>(RSJ-N-CethoxycarbonyO-S-C^K-^R^^hydroxy-i-methylethyllamino^delta-iodo- pyrimindin-2-yl]amino}phenyl)-S-methylsulfoximide (80 mg, 0.15 mmol), 1 H-pyrazol-5-yl-boronic acid (24.5 mg, 0.22 mmol), toluene (1.6 ml), ethanol (1.6 ml), palladium tetrakistriphenylphosphine (10.7 mg, 0.01 mmol) and sodium carbonate (0.3 ml, 1 M). are filled into a microwave tube and reacted under nitrogen for 15 mins at 120 0C. For the work-up, the reaction mixture is poured into dilute sodium carbonate solution and extracted with ethyl acetate (3x). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated under vacuum. After chromatographic purification, 30 mg (42percent) of the desired product are obtained.1H-NMR (DMSO): 12.99 (s, 1 H), 9.76 (s, 1 H), 8,78 (d, 1 H), 8,47 (s, 1 H), 8.05 (d, 2H), 7.78 (m, 3H), 6.79 (m, 1 H), 4.89 (t, 1 H), 4.31 (m, 1 H), 3.89 (m, 2H), 3.52 (m, 2H), 3.38 (s, 3H), 1.24 (2s, 3H), 1.07 (t, 3H). MS: 460 (MH+).
42% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 120℃; for 0.25h;Microwave irradiation; (RS)-N-(ethoxycarbonyl)-S-(4-[4-[(R)-2-(hydroxy-1-methylethyl]amino}-5-iodo-pyrimindin-2-yl]amino}phenyl)-S-methylsulfoximide (80 mg, 0.15 mmol), <strong>[376584-63-3]1H-pyrazol-5-yl-boronic acid</strong> (24.5 mg, 0.22 mmol), toluene (1.6 ml), ethanol (1.6 ml), palladium tetrakistriphenylphosphine (10.7 mg, 0.01 mmol) and sodium carbonate (0.3 ml, 1 M). are filled into a microwave tube and reacted under nitrogen for 15 mins at 120° C. For the work-up, the reaction mixture is poured into dilute sodium carbonate solution and extracted with ethyl acetate (3.x.). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated under vacuum. After chromatographic purification, 30 mg (42percent) of the desired product are obtained. 1H-NMR (DMSO): 12.99 (s, 1H), 9.76 (s, 1H), 8,78 (d, 1H), 8,47 (s, 1H), 8.05 (d, 2H), 7.78 (m, 3H), 6.79 (m, 1H), 4.89 (t, 1H), 4.31 (m, 1H), 3.89 (m, 2H), 3.52 (m, 2H), 3.38 (s, 3H), 1.24 (2s, 3H), 1.07 (t, 3H). MS: 460 (MH+).
  • 14
  • [ 939054-45-2 ]
  • [ 376584-63-3 ]
  • 1-isobutyl-6-(1H-pyrazol-5-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 170℃; for 0.333333h;Microwave irradiation; A mixture of compound 129 (90 mg), <strong>[376584-63-3]1H-pyrazol-5-ylboronic acid</strong> (60 mg), tetrakis(triphenylphosphine)palladium(0) (42 mg), 2M Na2CO3 (0.1 mL), ethanol (0.2 mL) and toluene (0.8 mL) was irradiated with microwaves (170° C., 20 min). Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified with HPLC to give the title compound (10 mg) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta 0.99 (d, J=6.57 Hz, 6H), 2.16-2.40 (m, 1H), 4.01 (dd, J=7.20, 5.94 Hz, 2H), 6.73 (br. s., 1H), 7.29-7.48 (m, 3H), 7.70 (d, J=7.33 Hz, 1H), 7.79-7.93 (m, 2H). [M+H] calc'd for C14H16N4 241; found, 241.
  • 15
  • [ 1032648-80-8 ]
  • [ 376584-63-3 ]
  • [ 1032648-68-2 ]
YieldReaction ConditionsOperation in experiment
36% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 120℃; for 2.5h;microwave irradiation; Example 31: l-[l-AUyl-6-(2H-pyrazol-3-yl)-lH-indol-3-yl]-2,2,2-tripiuoro-l-[l-(4- fluorophenyl)-lH-indazol-5-yl]ethanol; In a 10 mL microwave tube charged with 100.0 mg (0.18 mmol) of l-(l-allyl-6-bromo-lH- indol-3-yl)-2,2,2-trifluoro-l -[I -(4-fluorophenyl)- lH-indazol-5-yl]ethanol, 40.3 mg (0.36 mmol) of lH-pyrazole-5-boronic acid, 57.0 mg (0.53 mmol) of sodium carbonate, 23.1 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium, and 4 mL DMF was stirred in the microwave at 1200C for 2.5 hours. The mixture was then cooled to room temperature, quenched with saturated ammonia chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate-hexanes (30-80percent gradient). The major fractions were combined and concentrated in vacuo to afford 35.0 mg (36percent) of the title compound. MS m/z 532.5 (MH+).
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 376584-63-3 ]

Organoboron

Chemical Structure| 1314216-33-5

[ 1314216-33-5 ]

(1H-Pyrazol-3-yl)boronic acid hydrochloride

Similarity: 0.98

Chemical Structure| 869973-96-6

[ 869973-96-6 ]

(1-Methyl-1H-pyrazol-3-yl)boronic acid

Similarity: 0.88

Chemical Structure| 1163248-54-1

[ 1163248-54-1 ]

(5-Methyl-1H-pyrazol-3-yl)boronic acid

Similarity: 0.83

Chemical Structure| 844501-71-9

[ 844501-71-9 ]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.69

Chemical Structure| 1020174-04-2

[ 1020174-04-2 ]

1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.63

Related Parent Nucleus of
[ 376584-63-3 ]

Pyrazoles

Chemical Structure| 1314216-33-5

[ 1314216-33-5 ]

(1H-Pyrazol-3-yl)boronic acid hydrochloride

Similarity: 0.98

Chemical Structure| 869973-96-6

[ 869973-96-6 ]

(1-Methyl-1H-pyrazol-3-yl)boronic acid

Similarity: 0.88

Chemical Structure| 1163248-54-1

[ 1163248-54-1 ]

(5-Methyl-1H-pyrazol-3-yl)boronic acid

Similarity: 0.83

Chemical Structure| 844501-71-9

[ 844501-71-9 ]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.69

Chemical Structure| 1020174-04-2

[ 1020174-04-2 ]

1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.63

; ;