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[ CAS No. 914672-66-5 ]

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Chemical Structure| 914672-66-5
Chemical Structure| 914672-66-5
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CAS No. :914672-66-5 MDL No. :MFCD07368045
Formula : C14H23BN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :294.15 g/mol Pubchem ID :-
Synonyms :

Safety of [ 914672-66-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
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Application In Synthesis of [ 914672-66-5 ]

  • Downstream synthetic route of [ 914672-66-5 ]

[ 914672-66-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 914672-66-5 ]
  • [ 1312692-97-9 ]
  • [ 1312693-17-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube; 38 Preparation 38tert-Butyl 4-(6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-7-yl)-1H-pyrazole-1-carboxylate To an oven dried vial was added tert-butyl (1S,2R)-2-(7-iodo-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (40 mg, 0.069 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (30.6 mg, 0.104 mmol), and sodium carbonate (0.104 mL, 0.208 mmol) in DMF (1 mL). The resulting tan mixture was degassed 15 min. Bis(triphenylphosphine) palladium(II) chloride (4.86 mg, 6.93 μmol) was added and the mixture was degassed an additional 5 min. The vial was capped and was heated at 80° C. for 12 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with water (5 mL) and brine (5 mL). The organic layer was collected, dried with Na2SO4 and concentrated to give a brown residue, which was used without further purification (55 mg). LCMS indicated the desired mass less one of the Boc protecting groups. [M+H-Boc] calc'd for C33H43N7O5, 518. found, 518.
  • 2
  • [ 464192-28-7 ]
  • [ 914672-66-5 ]
  • 2-(1H-pyrazol-3-yl)thiazole-5-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 1h;Inert atmosphere; Step 1 : 2-(lH-pyrazol-3-yl) thiazole-5-carbaldehyde To a solution of <strong>[464192-28-7]2-bromothiazole-5-carbaldehyde</strong> (0.8 g, 4.16 mmol) in toluene (6 mL) and EtOH (5 mL), tert-butyl 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-pyrazole-l-carboxylate (1.8 g, 6.2 mmol), 2M a2C03 (6.2 mL, 12.4 mmol) and Pd(PPli3)4 (0.45 mg, 0.4 mmol) were added under argon. The mixture was degassed, heated to 100C, stirred for 1 h. After completion of the reaction, by monitoring with TLC (5% MeOHYDCM), the resulting mixture was filtered with Celite reagent and the filtrate was separated. This filtrate was concentrated, extracted with EtOAc (2x 100 mL), washed with water (100 mL), dried over Na2S04 and concentrated in vacuo. The resulting residue was purified by Biotage Isolera One column purifier (silica gel 100-200 microns) using 3% methanol in dichloromethane and isolated as yellow color solid (0.25 g, 33% yield).1H MR (400 MHz, DMSO-d6): ? 13.49 (brs, IH), 10.03 (s, IH), 8.60 (s, IH), 8.55 (s, IH), 8.09(s, IH); LC-MS m/z calcd for [M+H]+, 180.02; found, 180.1.
  • 3
  • [ 914672-66-5 ]
  • (S)-5-benzyl-N-(7-bromo-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-4H-1,2,4-triazole-3-carboxamide [ No CAS ]
  • (S)-5-benzyl-N-(2-oxo-7-(1H-pyrazol-3-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-4H-1,2,4-triazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 130℃; for 0.333333h; Microwave irradiation; 13.I Example 13 Method I (S)-5-benzyl-N-(2-oxo-7-(lH-pyrazol-3-yl)-2,3,4,5-tetrahydro-lH-benzo[b]azepin-3-yl)- - 1 ,2,4-triazole-3 -carboxamide (S)-5-benzyl-N-(7-bromo-2-oxo-2,3,4,5-tetrahydro-lH-benzo[b]azepin-3-yl)-4H- l,2,4-triazole-3 -carboxamide (60 mg, 0.136 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-pyrazole-l-carboxylate (40.1 mg, 0.136 mmol), Pd(PPh3)4 (29.8 mg, 0.026 mmol) and K2C03 (107 mg, 0.775 mmol) were mixed inl,4-dioxane (2 mL) and water (1 mL). The reaction mixture was put in an Emrys Optimizer (150W, absorption normal) and microwaved at 130 °C, for 20 min. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by reverse phase HPLC (Waters Sunfire 30x150mm, 26-60% CH3CN:H20 (0.1 % TFA), 50 mg/mL). Collected fractions containing the product were combined, neutralized by NaHC03, and then concentrated to give the desired product as a white solid (6 mg, 11 % yield). 1H MR (DMSO-d6) δ ppm 10.05 (s, 1H), 8.31 (br. s., 1H), 7.77 (s, 1H), 7.65 - 7.75 (m, 2H), 7.19 - 7.42 (m, 5H), 7.07 (d, J = 8.0 Hz, 1H), 6.71 (d, J = 1.5 Hz, 1H), 4.38 (dt, J = 11.2, 7.9 Hz, 1H), 4.12 (s, 2H), 2.66 - 2.90 (m, 2H), 2.42 - 2.51 (m, 1H), 2.28 (br. s., 1H); MS (m/z): 428 (M+H+).
  • 4
  • [ 914672-66-5 ]
  • 7’-[4-[4-(1,1-difluoroethyl)phenyl]-2,6-difluorophenyl]-3‘-iodospiro[cyclopropane-1,5’-imidazo[1,2-a]imidazole]-6’-one [ No CAS ]
  • tert-butyl 3-(1’-(4’-(1,1-difluoroethyl)-3,5-difluoro-[1,1‘-biphenyl]-4-yl)-2’-oxo-1‘,2’-dihydrospiro[cyclopropane-1,3’-imidazo[1,2-a]imidazol]-5‘-yl)-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 80℃; for 3h; D.1 Preparation of 3- [2,6-Difluoro-4-(2-phenylethynyi)phenyl] -6-phenyl-2,3- dihydrospir o [ [ 1 ,3] diazolo 1 ,2-a] imidazole- 1,1'- cyclopropane] -2-one General procedure: To a solution of 3'-[2,6-difluoro-4-(2-phenylethynyl)phenyl]-6'-iodo-2',3'- dihydrospiro[cyclopropane-l,l'- imidazo[l,2-a][l,3]diazole]-2'-one (Example 9) (50 mg, 0.103 mmol, 1 eq.) and phenyl boronic acid (18.8 mg, 0.154 mmol, 1.5 eq.) in DMF (2 ml) and H20 (0.5 ml) were added Na2C03 (53.9 mg, 0.513 mmol, 5 eq.) and PPh3 (10.8 mg, 0.041 mmol, 0.4 eq.) at 25°C and the reaction mixture was purged with argon for 10 min. Then Pd(OAc)2 (4.6 mg, 0.021 mmol, 0.2 eq.) was added and the reaction mixture again purged with argon for 10 min. The reaction mixture was stirred at 80°C for 3h, then cooled to 25°C, diluted with EtOAc and filtered through celite. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. The resulting crude was purified by prep-HPLC (NH4OAc/ CH3CN) to yield 3-[2,6-difluoro-4-(2-phenylethynyl)phenyl]-6-phenyl-2,3- dihydrospiro[[l,3]diazolo- [1,2-a imidazole- 1 , -cyclopropane] -2-one (4mg, 9%) as an off-white solid. M+H+ = 438.0.
  • 5
  • [ 914672-66-5 ]
  • (cis)-4-(3-bromo-4-methoxyphenyl)-2-isopropyl-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one [ No CAS ]
  • (cis)-2-isopropyl-4-(4-methoxy-3-(1H-pyrazol-3-yl)phenyl)-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 24h; Inert atmosphere;
  • 6
  • [ 914672-66-5 ]
  • 7-bromo-2-(3-(3,4-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine [ No CAS ]
  • 2-(3-(3 ,4-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-7-(1H-pyrazol-4-yl)-1,5-naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; 113 Example 113 Example 113 Synthesis of 2-(3-(3 ,4-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-7-(1H-pyrazol-4-yl)-1,5-naphthyridine (135) A mixture of Compound 131 (1.5 g, 3.18 mmol), compound 134 (4.0 g, 9.55 mmol), Pd(dppf)Cl2 (466 mg, 0.637 mmol) and K2CO3 (880 mg, 6.37 mmol) in dioxane (20 mL) and H2O (4 mL) was stirred at 100° C. under N2 for 16 h. The mixture was combined with two additional reactions. The combined mixture was concentrated under reduced pressure. The residue was purified by column to give product 135 as light yellow solid (1.2 g, 59% yield, 97% purity). [M+H]+ calcd for C25H20F2N6O 459.17, found 459.3. 1H NMR (400 MHz, Chloroform-d) δ 9.12 (d, J=2.2 Hz, 1H), 8.42 (t, J=2.2, 0.9 Hz, 1H), 8.32 (s, 1H), 8.21 (dd, J=8.8, 0.9 Hz, 1H), 8.09 (s, 2H), 7.76-7.65 (m, 2H), 7.38 (t, J=8.8 Hz, 1H), 5.55 (dd, J=6.9, 5.5 Hz, 1H), 4.21-4.13 (m, 1H), 3.78 (td, J=11.0, 3.0 Hz, 1H), 2.22 (q, J=5.6, 4.7 Hz, 2H), 2.11 (s, 2H), 1.88-1.50 (m, 2H).
  • 7
  • [ 24424-99-5 ]
  • [ 914672-66-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / tetrahydrofuran / 3 h / 15 °C / Inert atmosphere 2: isopropylmagnesium chloride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere
  • 8
  • [ 121669-70-3 ]
  • [ 61676-62-8 ]
  • [ 914672-66-5 ]
YieldReaction ConditionsOperation in experiment
With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere; 112 Example 112: Synthesis of tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (134) To a mixture of compound 133 (23.8 g, 80.9 mmol), i-PrOBPin (22.6 g, 121 mmol) in THF (300 mL) was added i-PrMgCl (81 mL, 162 mmol) at 0° C. The reaction was stirred at 20° C. for 3.5 h. The reaction was quenched with H2O (50 mL), extracted with DCM (2×300 mL). The combined organic layer was dried over Na2SO4, concentrated under reduced pressure and dried in vacuum to give crude produce 134, used directly in next step as white solid (20.0 g, 60% yield, 71% purity).
  • 9
  • [ 914672-66-5 ]
  • 7-bromo-2-(3-(3-(methoxymethyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine [ No CAS ]
  • 2-(3-(3-(methoxymethyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-7-(1H-pyrazol-4-yl)-1,5-naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium <i>tert</i>-butylate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere; 152 Example 152: Synthesis of 2-(3-(3-(methoxymethyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-7-(1H-pyrazol-4-yl)-1,5-naphthyridine (169) To a solution of 168 (970 mg, 2.02 mmol), t-BuOK (680 mg, 6.06 mmol) and 134 (3.6 g, 12.1 mmol) in dioxane (20 mL) and H2O (2 mL) was added Pd(dppf)Cl2 (739 mg, 1.01 mmol) under N2. The reaction mixture was stirred at 100° C. for 12 h. The mixture was filtered and concentrated in vacuum to give the residue. The residue was purified by silica column (PE:EA=1:1 to 0:1) and prep-HPLC (Xtimate C18 10 μm, 250 mm×50 mm, water (0.5% ammonia hydroxide v/ v-ACN, 32% to 62% MeCN in H2O) to afford 169 as yellow solid (460 mg, 42% yield, 100% purity). [M+H]+ calcd for C27H26N6O2 467.22, found 467.3. [M+H]+ calcd for C27H26N6O2 467.22, found 467.3. 1H NMR (400 MHz, DMSO-d6) δ 13.17 (s, 1H), 9.29 (d, J=2.2 Hz, 1H), 8.54 (s, 1H), 8.47-8.38 (m, 3H), 8.26 (d, J=8.8 Hz, 1H), 7.64-7.54 (m, 2H), 7.48 (dt, J=7.5, 1.7 Hz, 1H), 7.45-7.32 (m, 2H), 5.56 (dd, J=10.0, 2.4 Hz, 1H), 4.42 (s, 2H), 4.06-3.96 (m, 1H), 3.73 (dd, J=9.3, 4.9 Hz, 1H), 3.24 (s, 3H), 2.21 (q, J=9.4 Hz, 1H), 2.10-1.96 (m, 2H), 1.74 (s, 1H), 1.60 (dt, J=9.3, 5.3 Hz, 2H).).
  • 10
  • [ 914672-66-5 ]
  • 2-(4-(5-bromo-1H-benzo[d]imidazol-1-yl)phenyl)-N-(isoxazol-5-yl)acetamide [ No CAS ]
  • 2-(4-(5-(1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-N-(isoxazol-5-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 65 - 90℃; Inert atmosphere; 1 General procedure: Under nitrogen protection, compound 8 (0.77mmol), boric acid derivative 9 or borate derivative 10 (0.93mmol), Pd(dppf)Cl2 (28mg, 0.039mmol), Na2CO3 (1.2ml, 2.32mmol, 2N aqueous solution) The mixed solution of) and dioxane (3mL) was stirred at 65-90°C for 6-10 hours, until TLC monitoring of the reaction showed that compound 8 was completely consumed, the reaction mixture was cooled to room temperature, ethyl acetate (15mL×3) After extraction, the organic phase was washed with water and brine, dried over anhydrous Na2SO4 and evaporated to dryness to obtain a crude product, which was purified by preparative thin-layer chromatography to obtain a medium to good yield. Specifically, the characterization results of each embodiment and the target product are as follows:
  • 11
  • [ 914672-66-5 ]
  • [ 170456-80-1 ]
  • 3-(1H-pyrazol-3-yl)-1-tosyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; Cs2CO3 In 1,4-dioxane; lithium hydroxide monohydrate at 110℃; Inert atmosphere; 13 Preparative Example 13: 3-(1H-pyrazol-3-yl)-1-tosyl-1H-indole To a mixture of 3-iodo-1-tosyl-1 H-indole (900 mg, 2.266 mmol) and tert-butyl 3-(4,4,5,5-tetramethyl-1 , 3, 2-dioxaborolan-2-yl)-1 H-pyrazole-1 -carboxylate (666 mg, 2.266 mmol) in 1 ,4-dioxane (20 ml) and water (3 ml), was added 1 ,T-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane (93 mg, 0.113 mmol) and cesium carbonate (1846 mg, 5.66 mmol). The mixture was degassed and filled with N2and stirred under N2atmosphere at 110°C overnight. The reaction mixture was filtered through celite and washed with DCM (100 ml) and MeOH (20 ml) and concentrated under reduced pressure. The crude was purified on silica gel column using Biotage Isolera One purification system employing an EtOAc/hexane gradient (60/40) to afford the title compound (600 mg, 75 %) as a pale brown solid. MS: 338.0 (M+H)+.
75% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; Cs2CO3 In 1,4-dioxane; lithium hydroxide monohydrate at 110℃; Inert atmosphere; 13 Preparative Example 13: 3-(1H-pyrazol-3-yl)-1-tosyl-1H-indole To a mixture of 3-iodo-1-tosyl-1 H-indole (900 mg, 2.266 mmol) and tert-butyl 3-(4,4,5,5-tetramethyl-1 , 3, 2-dioxaborolan-2-yl)-1 H-pyrazole-1 -carboxylate (666 mg, 2.266 mmol) in 1 ,4-dioxane (20 ml) and water (3 ml), was added 1 ,T-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane (93 mg, 0.113 mmol) and cesium carbonate (1846 mg, 5.66 mmol). The mixture was degassed and filled with N2and stirred under N2atmosphere at 110°C overnight. The reaction mixture was filtered through celite and washed with DCM (100 ml) and MeOH (20 ml) and concentrated under reduced pressure. The crude was purified on silica gel column using Biotage Isolera One purification system employing an EtOAc/hexane gradient (60/40) to afford the title compound (600 mg, 75 %) as a pale brown solid. MS: 338.0 (M+H)+.
  • 12
  • [ 914672-66-5 ]
  • 3-bromo-1-tosyl-1H-indazole [ No CAS ]
  • 3-(1H-pyrazol-3-yl)-1-tosyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 16.0833h; Sealed tube; Inert atmosphere; 12 Preparative Example 12: 3-(1H-pyrazol-3-yl)-1-tosyl-1H-indazole In a sealed tube (50 ml), a solution of 3-bromo-1-tosyl-1 H-indazole (1 g, 2.85 mmol) and tert-butyl 3-(4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolan-2-yl)-1 H-pyrazole-1 -carboxylate (0.838 g, 2.85 mmol) were dissolved in 1 ,4-dioxane (6 ml) and water (2 ml). Nitrogen gas was bubbled through the mixture for a period of 5 minutes. Then, Tetrakis(triphenylphosphine)palladium(0) (0.165 g, 0.142 mmol) and sodium carbonate (0.754 g, 7.12 mmol) were added under nitrogen atmosphere. The reaction mixture was heated at 100°C for 16 hours. The mixture was concentrated under reduced pressure and was purified on silica gel column using Biotage Isolera One purification system eluting with EtOAcZ petroleum ether (50/50) to afford the title compound (0.5 g, 49%) as a pale brown solid.
49% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 16.0833h; Sealed tube; Inert atmosphere; 12 Preparative Example 12: 3-(1H-pyrazol-3-yl)-1-tosyl-1H-indazole In a sealed tube (50 ml), a solution of 3-bromo-1-tosyl-1 H-indazole (1 g, 2.85 mmol) and tert-butyl 3-(4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolan-2-yl)-1 H-pyrazole-1 -carboxylate (0.838 g, 2.85 mmol) were dissolved in 1 ,4-dioxane (6 ml) and water (2 ml). Nitrogen gas was bubbled through the mixture for a period of 5 minutes. Then, Tetrakis(triphenylphosphine)palladium(0) (0.165 g, 0.142 mmol) and sodium carbonate (0.754 g, 7.12 mmol) were added under nitrogen atmosphere. The reaction mixture was heated at 100°C for 16 hours. The mixture was concentrated under reduced pressure and was purified on silica gel column using Biotage Isolera One purification system eluting with EtOAcZ petroleum ether (50/50) to afford the title compound (0.5 g, 49%) as a pale brown solid.
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Chemical Structure| 1402174-61-1

[ 1402174-61-1 ]

tert-Butyl 5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Similarity: 0.88

Chemical Structure| 1162261-97-3

[ 1162261-97-3 ]

(1-(tert-Butoxycarbonyl)-1H-pyrazol-3-yl)boronic acid

Similarity: 0.82