Home Cart 0 Sign in  

[ CAS No. 1312312-78-9 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1312312-78-9
Chemical Structure| 1312312-78-9
Structure of 1312312-78-9 * Storage: {[proInfo.prStorage]}

Quality Control of [ 1312312-78-9 ]

Related Doc. of [ 1312312-78-9 ]

SDS
Alternatived Products of [ 1312312-78-9 ]
Alternatived Products of [ 1312312-78-9 ]

Product Details of [ 1312312-78-9 ]

CAS No. :1312312-78-9 MDL No. :MFCD16995953
Formula : C13H18BN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :259.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1312312-78-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1312312-78-9 ]

  • Downstream synthetic route of [ 1312312-78-9 ]

[ 1312312-78-9 ] Synthesis Path-Downstream   1~25

YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 2-methyltetrahydrofuran at 120℃; for 3h; Inert atmosphere; Sealed tube; 2.ii Example 2 General Preparation of the Ring A Intermediates of Formula O General procedure: As shown in step 2-ii of Scheme 2, A solution of the 5-bromo-pyrazolo[3,4-b]pyridine of formula N (1 equiv.), bis-pinacol borane (1.15 equiv.), KOAc (3 equiv.) in 2-methyl-THF (0.3 M) was degassed with a stream of N2 for 20 min. Then, Pd(dppf)Cl2 (0.05 equiv.) was added to the reaction mixture. The resulting solution was heated in a sealed tube at 120° C. for 3 h in an oil bath. The solution was cooled down to room temperature and filtered over a pad of Florisil. The filtrate was evaporated and the resulting compound of formula 0 was produced. In many cases, these compounds could be subsequently used without any further purification. The procedure of Example 2 can be followed to prepare the following compounds.
  • 2
  • [ 1312312-78-9 ]
  • 4-(5-chloro-8-(4-(dimethylamino)piperidin-1-yl)imidazo[1,2-a]pyrazin-6-yl)benzonitrile [ No CAS ]
  • [ 76-05-1 ]
  • 4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzonitrile trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazolo[3,4-b]pyridine; 4-(5-chloro-8-(4-(dimethylamino)piperidin-1-yl)imidazo[1,2-a]pyrazin-6-yl)benzonitrile With potassium phosphate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium(II) In 1,4-dioxane; water at 90℃; for 2h; Sealed tube; Stage #2: trifluoroacetic acid In water; acetonitrile 58.5 Step 5: A degassed solution of 4-{5-chloro-8-[4-(dimethylamino)piperidin-1-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile (10 mg, 0.03 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (Advance ChemBlocks, cat No.I-9516: 8.8 mg, 0.034 mmol), potassium phosphate (20 mg, 0.1 mmol) and dichloro[1,1'-bis(dicyclohexylphosphino)ferrocene]palladium(II) (2 mg, 0.003 mmol) in a mixed solvent of 1,4-dioxane (1 mL) and water (0.15 mL) was heated in a sealed vial at 90° C. for 2 h. After cooling to room temperature, the mixture was concentrated, diluted with MeOH, filtered then purified by prep-HPLC (pH=2, acetonitrile/water+TFA) to give the desired product as the TFA salt. LC-MS calculated for C27H28N9 (M+H)+: m/z=478.2. found 478.2.
  • 3
  • [ 1312312-78-9 ]
  • tert-butyl (3R)-3-[(5-bromo-6-chloroimidazo[1,5-a]pyrazin-8-yl)oxy]methyl}piperidine-1-carboxylate [ No CAS ]
  • [ 126747-14-6 ]
  • tert-butyl (3R)-3-([6-(4-cyanophenyl)-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,5-a]pyrazin-8-yl]oxy}methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazolo[3,4-b]pyridine; tert-butyl (3R)-3-[(5-bromo-6-chloroimidazo[1,5-a]pyrazin-8-yl)oxy]methyl}piperidine-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere; Stage #2: 4-cyanophenylboronic acid With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II); caesium carbonate In <i>tert</i>-butyl alcohol at 90℃; for 1h; Inert atmosphere; 37.1 Step 1: tert-butyl (3R)-3-([6-(4-cyanophenyl)-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,5-a]pyrazin-8-yl]oxy}methyl)piperidine-1-carboxylate A mixture of tert-butyl (3R)-3-[(5-bromo-6-chloroimidazo[1,5-a]pyrazin-8-yl)oxy]methyl}piperidine-1-carboxylate (Example 21, Step 5: 140 mg, 0.31 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (98 mg, 0.38 mmol) [Advanced ChemBlocks Inc, catI-9516], tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol) and potassium carbonate (130 mg, 0.94 mmol) in 1,4-dioxane (3.5 mL) and water (0.7 mL) was purged with nitrogen and then stirred at 100° C. for 2 hours. After cooling to room temperature, (4-cyanophenyl)boronic acid (69 mg, 0.47 mmol), dichloro[1,1′-bis(dicyclohexylphosphino)ferrocene]palladium(II) (20 mg, 0.03 mmol), and cesium carbonate (200 mg, 0.63 mmol) and tert-butyl alcohol (3 mL) were added the reaction mixture. The resulting mixture was purged with nitrogen and stirred at 90° C. for 1 hour. After cooling to room temperature, the mixture was concentrated and purified by flash chromatography eluting with 0 to 5% MeOH in DCM to give the desired product. LC-MS calculated for C31H32N8O3 (M+H)+: m/z=565.2. found 565.3
  • 4
  • [ 1312312-78-9 ]
  • 1-(5-bromo-6-chloroimidazo[1,5-a]pyrazin-8-yl)-N,N-dimethylpiperidin-4-amine [ No CAS ]
  • [ 126747-14-6 ]
  • [ 76-05-1 ]
  • 4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,5-a]pyrazin-6-yl]benzonitrile trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazolo[3,4-b]pyridine; 1-(5-bromo-6-chloroimidazo[1,5-a]pyrazin-8-yl)-N,N-dimethylpiperidin-4-amine With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere; Stage #2: 4-cyanophenylboronic acid With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II); caesium carbonate In 1,4-dioxane; water; <i>tert</i>-butyl alcohol at 90℃; for 1h; Inert atmosphere; Stage #3: trifluoroacetic acid In water; acetonitrile 50.2 Step 2: 4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl) imidazo[1,5-a]pyrazin-6-yl]benzonitrile General procedure: A mixture of 1-(5-bromo-6-chloroimidazo[1,5-a]pyrazin-8-yl)-N,N-dimethylpiperidin-4-amine (30 mg, 0.08 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (Advanced ChemBlocks Inc, cat I-9516: 20 mg, 0.08 mmol), tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.008 mmol) and potassium carbonate (30 mg, 0.2 mmol) in 1,4-dioxane (910 μL) and water (200 μL) was purged with nitrogen and then stirred at 100° C. for 2 hours. The reaction mixture was cooled to room temperature then (4-cyanophenyl)boronic acid (18 mg, 0.12 mmol), dichloro[1,1′-bis(dicyclohexylphosphino)ferrocene]palladium(II) (6 mg, 0.008 mmol), cesium carbonate (50 mg, 0.2 mmol) and tert-butyl alcohol (0.7 mL) were added. The resulting mixture was purged with nitrogen and stirred at 90° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with methanol then purified by prep-HPLC (pH=2, acetonitrile/water+TFA) to give the desired product as the TFA salt. LC-MS calculated for C27H28N9(M+H)+: m/z=478.2. found 478.2. 1H NMR (500 MHz, CD3OD) δ 8.42 (d, J=2.0 Hz, 1H), 8.40 (d, J=2.0 Hz, 1H), 8.22 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.57-7.49 (m, 4H), 4.97-4.89 (m, 2H), 4.14 (s, 3H), 3.67-3.56 (m, 1H), 3.31-3.24 (m, 2H), 2.93 (s, 6H), 2.30-2.21 (m, 2H), 1.95-1.83 (m, 2H).
  • 5
  • [ 1312312-78-9 ]
  • 4-{8-bromo-5-[4-(dimethylamino)piperidin-1-yl]imidazo[1,2-c]pyrimidin-7-yl}benzonitrile [ No CAS ]
  • [ 76-05-1 ]
  • 4-[5-[4-(dimethylamino)piperidin-1-yl]-8-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazolo[3,4-b]pyridine; 4-{8-bromo-5-[4-(dimethylamino)piperidin-1-yl]imidazo[1,2-c]pyrimidin-7-yl}benzonitrile With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); sodium carbonate In water; <i>tert</i>-butyl alcohol at 95℃; for 3h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile; <i>tert</i>-butyl alcohol 37.2 Step 2: 4-[5-[4-(dimethylamino)piperidin-1 -yl]-8-(1 -methyl-H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[ 1,2- c]pyrimidin-7-yl]benzonitrile Step 2: 4-[5-[4-(dimethylamino)piperidin-1-yl]-8-(1-methyl-H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile A mixture of 1-methyl-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (PharmaBlock, catNo.PB02930: 366 mg, 1.41 mmol), 4-{8-bromo-5-[4-(dimethylamino)piperidin-1-yl]imidazo[1,2-c]pyrimidin-7-yl}benzonitrile (300 mg, 0.71 mmol), sodium carbonate (150 mg, 1.41 mmol), and dichloro[1,1'-bis(dicyclohexylphosphino)ferrocene]palladium(II) (53 mg, 0.07 mmol) in tert-butyl alcohol (10 mL) and water (6 mL) was first purged with nitrogen, then heated to 95° C. and stirred for 3 h. The reaction mixture was cooled to room temperature then purified by prep-HPLC (pH=2, acetonitrile/water+TFA) to give the desired product as the TFA salt. LC-MS calculated for C27H28N9(M+H)+: m/z=478.2. found 478.2. 1H NMR (400 MHz, CD3OD) δ 8.38 (d, J=2.0 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.18 (d, J=2.1 Hz, 1H), 8.15 (s, 1H), 7.97 (d, J=2.1 Hz, 1H), 7.67-7.57 (m, 4H), 4.43-4.33 (m, 2H), 4.14 (s, 3H), 3.69-3.57 (m, 1H), 3.41-3.32 (m, 2H), 2.96 (s, 6H), 2.36-2.26 (m, 2H), 2.19-2.05 (m, 2H).
  • 6
  • [ 1312312-78-9 ]
  • tert-butyl (3R)-3-([8-bromo-7-(4-cyanophenyl)imidazo[1,2-c]pyrimidin-5-yl]oxy}methyl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl (3R)-3-([7-(4-cyanophenyl)-8-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl) imidazo[1,2-c]pyrimidin-5-yl]oxy}methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); sodium carbonate In water; <i>tert</i>-butyl alcohol at 105℃; for 2h; Inert atmosphere; 29.1 Step 1: tert-butyl (3R)-3-({ [7-(4-cyanophenyl)-8-(i - methyl-i H-pyrazolo[3,4-b]pyridin-5-yl) imidazo[ 1, 2-c]pyrimidin-5-yl]oxy}methyl)piperidine- i-carboxylate Step 1: tert-butyl (3R)-3-([7-(4-cyanophenyl)-8-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl) imidazo[1,2-c]pyrimidin-5-yl]oxy}methyl)piperidine-1-carboxylate A mixture of 1-methyl-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (PharmaBlock, catNo.PB02930: 127 mg, 0.492 mmol), tert-butyl (3R)-3-([8-bromo-7-(4-cyanophenyl)imidazo[1,2-c]pyrimidin-5-yl]oxy}methyl)piperidine-1-carboxylate (prepared in Example 1, Step 5: 126 mg, 0.246 mmol), sodium carbonate (52.1 mg, 0.492 mmol), and dichloro[1,1'-bis(dicyclohexylphosphino)ferrocene]palladium(II) (19 mg, 0.024 mmol) in tert-butyl alcohol (4 mL) and water (2 mL) was first purged with nitrogen, then stirred and heated at 105° C. for 2 h. The reaction mixture was cooled to room temperature then diluted with methylene chloride, washed with saturated NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 10% MeOH in methylene chloride to give the desired product (119 mg, 86%). LCMS calculated for C31H33N8O3 (M+H)+: m/z=565.3. found 565.2.
  • 7
  • [ 887115-56-2 ]
  • [ 73183-34-3 ]
  • [ 1312312-78-9 ]
YieldReaction ConditionsOperation in experiment
13.5 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃; for 8h;Inert atmosphere; Step 2 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (compound 4-3) Compound 4-2 (3.1 g, 14.6 mmol) and bis(pinacolato) borate (11.1 g, 43.8 mmol) were added into a 250 ml reaction flask, and DMF (150 ml) and potassium acetate (4.3 g, 43.8 mmol) was added. After the air of reaction system was replaced by argon for three times, Pd(dppf)Cl2 (0.55 g, 0.73 mmol) was added, and then the air was replaced with nitrogen for another three times. The reaction system was heated to 90 C., and stirred for 8 h. The reaction progress was monitored by LC-MS. After completion of the reaction, the reaction solution was filtered, the filter cake was washed with EA (30 ml*3), and the filtrate was concentrated under reduced pressure to remove DMF and give compound 4-3 (13.5 g) as brown solid which was used directly in next reaction. MS m/z (ESI): 260.2 [M+H]+.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 1h; A mixture of <strong>[887115-56-2]5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine</strong> (3.04 g, 14.0 mmol), bis(pinacolato)diboron (4.37 g, 17.0 mmol), PdCl2(dppf) (0.992 g, 1 mmol), and potassium acetate (3.52 g, 36 mmol) in dioxane was heated at 100 C. for 1 hour. Reaction mixture was portioned between ethyl acetate and saturated sodium bicarbonate solution, organic layer dried (MgSO4), filtered, concentrated and purified by CombiFlash (ethyl acetate/hexanes) to give desired product. LCMS-ESI+: calc'd for C13H19BN3O2: 260.2 (M+H)+; found: 260.2 (M+H)+.
  • 8
  • [ 875781-17-2 ]
  • [ 1312312-78-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 25 °C / Inert atmosphere 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 8 h / 90 °C / Inert atmosphere
  • 9
  • [ 1312312-78-9 ]
  • N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 3 h / 85 °C / Inert atmosphere 2: toluene-4-sulfonic acid / 2-methyl-propan-1-ol / 16 h / 130 °C / Sealed tube; Inert atmosphere
  • 10
  • [ 1312312-78-9 ]
  • N-(4-(4-(dimethylamino)piperidin-1-yl)-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 3 h / 85 °C / Inert atmosphere 2: toluene-4-sulfonic acid / 2-methyl-propan-1-ol / 16 h / 130 °C / Sealed tube; Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere
  • 11
  • [ 1312312-78-9 ]
  • N-(2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl)-4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 3 h / 85 °C / Inert atmosphere 2: toluene-4-sulfonic acid / 2-methyl-propan-1-ol / 16 h / 130 °C / Sealed tube; Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere
  • 12
  • [ 1312312-78-9 ]
  • N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 3 h / 85 °C / Inert atmosphere 2: toluene-4-sulfonic acid / 2-methyl-propan-1-ol / 16 h / 130 °C / Sealed tube; Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere
  • 13
  • [ 3934-20-1 ]
  • [ 1312312-78-9 ]
  • 5-(2-chloropyrimidin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In acetonitrile at 85℃; for 3h; Inert atmosphere; 4.3 Step 3
5-(2-chloropyrimidin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine (Compound 4-4) Step 3 5-(2-chloropyrimidin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine (Compound 4-4) The reaction substrate 4-3 (3.8 g, 14.6 mmol) and 2,4-dichloropyrimidine (2.6 g, 17.5 mmol) were added into a 250 ml reaction flask, and acetonitrile (130 ml) and sodium carbonate solution (22 mL, 2M) were added. After the air of reaction system was replaced by argon for three times, Pd(dppf)Cl2 (0.55 g, 0.73 mmol) was added, and then the air was replaced with nitrogen for another three times. The reaction system was heated to 85° C., and stirred continuously for 3 h. The reaction progress was monitored by LC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature and large amount of solids precipitated, and filtered, the filter cake was washed with EA (10 ml*3) and dried to constant weight to give 2.2 g yellow solid, and the filtrate was extracted with EA and water, dried, concentrated, and then purified by Combi-flash chromatography [PE:EA=10:90-70:30] to get 0.6 g yellow solids. The solids were combined to give the title compound 4-4 (2.8 g, 78%). MS m/z (ESI): 246.1 [M+H]+
  • 14
  • [ 1312312-78-9 ]
  • ethyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • ethyl (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 100℃; for 1h; 111 Preparation of ethyl (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate A mixture of ethyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate (3.84 g, 8.0 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (2.0 g, 8.0 mmol), Pd(PPh3)4(0.446 g, 0.39 mmol) in 2M potassium carbonate solution (7.72 mL, 15 mmol) and dioxane (40 mL) was heated at 100° C. for 1 hour. Reaction was stopped, reaction mixture was portioned between ethyl acetate and saturated sodium bicarbonate solution, organic layer dried (MgSO4), filtered, concentrated and purified by CombiFlash (ethyl acetate/hexanes) to give desired product. LCMS-ESI+: calc'd for C29H30ClN4O3S: 549.2 (M+H)+; found: 549.2.
  • 15
  • [ 1312312-78-9 ]
  • ethyl (S)-2-(2-(3-(1-(azetidin-3-yl)piperidin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol 5: hydrogenchloride / isopropyl alcohol / 28 h 6: acetic acid; sodium cyanoborohydride / methanol 7: hydrogenchloride / isopropyl alcohol / 48 h
  • 16
  • [ 1312312-78-9 ]
  • methyl (S)-3-(4-(5-(6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidin-1-yl)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol 5: hydrogenchloride / isopropyl alcohol / 28 h 6: acetic acid; sodium cyanoborohydride / methanol 7: hydrogenchloride / isopropyl alcohol / 48 h 8: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C
  • 17
  • [ 1312312-78-9 ]
  • ethyl (S)-2-(2-(3-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile
  • 18
  • [ 1312312-78-9 ]
  • ethyl (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-2-(3-(4-isopropylpiperazin-1-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C
  • 19
  • [ 1312312-78-9 ]
  • (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-2-(3-(4-isopropylpiperazin-1-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C 4: ethanol; sodium hydroxide / N,N-dimethyl-formamide / 1 h / 60 °C
  • 20
  • [ 1312312-78-9 ]
  • tert-butyl (S)-4-(5-(6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C
  • 21
  • [ 1312312-78-9 ]
  • tert-butyl (S)-4-(5-(6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol
  • 22
  • [ 1312312-78-9 ]
  • ethyl (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(piperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol 5: hydrogenchloride / isopropyl alcohol / 28 h
  • 23
  • [ 1312312-78-9 ]
  • ethyl (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-(oxetan-3-yl)piperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol 5: hydrogenchloride / isopropyl alcohol / 28 h 6: acetic acid; sodium cyanoborohydride / methanol
  • 24
  • [ 1312312-78-9 ]
  • (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-(oxetan-3-yl)piperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol 5: hydrogenchloride / isopropyl alcohol / 28 h 6: acetic acid; sodium cyanoborohydride / methanol 7: ethanol; sodium hydroxide / tetrahydrofuran / 40 °C
  • 25
  • [ 1312312-78-9 ]
  • tert-butyl (S)-3-(4-(5-(6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidin-1-yl)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 100 °C 2: bromine / acetonitrile 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / 100 °C 4: hydrogen; Rh/Al2O3 / ethanol 5: hydrogenchloride / isopropyl alcohol / 28 h 6: acetic acid; sodium cyanoborohydride / methanol
Historical Records

Related Functional Groups of
[ 1312312-78-9 ]

Organoboron

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89

Chemical Structure| 1314137-24-0

[ 1314137-24-0 ]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.83

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89

Organoboron

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89

Chemical Structure| 1314137-24-0

[ 1314137-24-0 ]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.83

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89

Esters

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| N/A

[ N/A ]

1,3-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.90

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| N/A

[ N/A ]

1,3-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.90

Related Parent Nucleus of
[ 1312312-78-9 ]

Other Aromatic Heterocycles

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89

Chemical Structure| 1314137-24-0

[ 1314137-24-0 ]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.83

Chemical Structure| 1809889-70-0

[ 1809889-70-0 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazolo[3,4-b]pyridine

Similarity: 0.96

Chemical Structure| 1093819-50-1

[ 1093819-50-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Similarity: 0.89