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[ CAS No. 942070-38-4 ]

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Chemical Structure| 942070-38-4
Chemical Structure| 942070-38-4
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CAS No. :942070-38-4 MDL No. :MFCD11855974
Formula : C17H26BNO6 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :351.20 g/mol Pubchem ID :-
Synonyms :

Safety of [ 942070-38-4 ]

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 [ 942070-38-4 ]

  • Downstream synthetic route of [ 942070-38-4 ]

[ 942070-38-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 942070-38-4 ]
  • [ 1198605-53-6 ]
YieldReaction ConditionsOperation in experiment
99% at 180℃; for 0.3h; 38 Compound 38F: Methyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2- carboxylate1-Soc-2-(methoxycarbonyl)pyrrole-4-boronic acid, pinacol ester (900 mg, 2.56 mmol) was heated at 180 °C for 18 min to afford 0.643 mg of the title compound which was used without further purification (99%). 1H NMR (400 MHz, CD3OD) δ 7.27 (d, J = 1.5 Hz, 1 H), 7.10 (d, J = 1.3 Hz, 1 H), 3.82 (s, 3H), 1.31 (s, 12H). MS (ESI): m/z 252.13 [M+H]+. HPLC: tR = 1 .32-TOF: polar_3 min).
76% at 180℃; for 0.3h;
2.5 g With zinc dibromide In acetonitrile at 50℃; for 4h; 4.1 Example 4: Preparation of 4-(3-methyl-pyridin-4-yl)-lH-pyrrole-2-carboxylic acid amide Step 1: Preparation of 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrrole-2- carboxylic acid methyl ester To a mixture of 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-pyrrole-l,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (10 g, 28.5 mmol) in MeCN (50 mL) was added ZnBr2 (12.8 g, 57 mmol) at room temperature. The mixture was heated at 50 °C for 4 hours, and then quenched with water (30 mL) and then basified to pH 9 with aqueous ammonia. The aqueous layer was extracted with EtOAc (30 mLx 3). The combined organic layers were dried over anhydrous Na2S04 and then concentrated. The residue was purified by column chromatography to give 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrrole-2-carboxylic acid methyl ester as a white solid (2.5 g).
  • 2
  • [ 25015-63-8 ]
  • [ 294659-30-6 ]
  • [ 942070-38-4 ]
YieldReaction ConditionsOperation in experiment
75% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 5h; Inert atmosphere; regioselective reaction;
72% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 80℃; Sealed tube; Inert atmosphere; regioselective reaction;
  • 3
  • 4-((2-chloropyridin-4-yl)oxy)aniline [ No CAS ]
  • [ 942070-38-4 ]
  • [ 1268621-47-1 ]
YieldReaction ConditionsOperation in experiment
86% With sodium carbonate In 1,4-dioxane at 70℃; for 0.5h; 142 Preparation of 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate Preparation of 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate A 100 ml flask was charged with 4-((2-chloropyridin-4-yl)oxy)aniline (150 mg, 0.68 mmol), 1-tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate (260 mg, 0.81 mmol), 2M Na2CO3 solution (0.5 ml, 1.0 mmol), PdCl2(PPh3)2 (5 mg, 0.007 mmol), 10 ml of 1,4-dioxane and 3 ml of water. The mixture was flushed with nitrogen and heated at 70° C. for 30 minutes. The mixture was cooled to room temperature and poured into 100 ml of water. The precipitates were filtered and dried to give the crude, which was further purified by silica gel chromatography eluding with 2-3% MeOH/CHCl3 to give 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate as light brown oil. Yield: 240 mg, 86%.
86% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 70℃; for 0.5h; Inert atmosphere; Preparation of 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2- dicarboxylate Preparation of 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2- dicarboxylateA 100ml flask was charged with 4-((2-chloropyridin-4-yl)oxy)aniline (150mg, 0.68mmol), 1- tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2- dicarboxylate (260mg, 0.81mmol), 2M Na2CO3 solution (0.5ml, 1.0mmol), PdCl2(PPh3)2 (5mg, 0.007mmol), 10ml of 1,4-dioxane and 3ml of water. The mixture was flushed with nitrogen and heated at 70C for 30 minutes. The mixture was cooled to room temperature and poured into 100ml of water. The precipitates were filtered and dried to give the crude, which was further purified by silica gel chromatography eluting with 2-3% MeOH/CHCl3 to give 1-tert-butyl 2- methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate as light brown oil. Yield: 240mg, 86%.
  • 4
  • [ 942070-38-4 ]
  • [ 1380306-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 0.3 h / 180 °C 2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C 3: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation 4: 5% Pd-CaCO3 / palladium 10% on activated carbon / ethanol / 16 h / 20 °C
  • 5
  • [ 942070-38-4 ]
  • [ 1380306-56-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 0.3 h / 180 °C 2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C 3: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation
  • 6
  • [ 942070-38-4 ]
  • [ 1380306-60-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.3 h / 180 °C 2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C
  • 7
  • [ 942070-38-4 ]
  • [ 1287793-22-9 ]
  • [ 1287793-23-0 ]
YieldReaction ConditionsOperation in experiment
48% With caesium carbonate In 1,2-dimethoxyethane; water for 16h; Reflux; 76 Example 76 7-(5-carboxy-1H-pyrrol-3-yl)-2-(3-fluorophenyl)-2H-[1,2,3]-triazolo[4,5-f]quinoline-9-carboxylic acid (Compound 76) Compound 75 (60 mg, 0.18 mmol) obtained in Example 75, 1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)pyrrole-4-boronic acid pinacol ester (92 mg, 0.26 mmol), and cesium carbonate (171 mg, 0.53 mmol) were dissolved in a mixed solvent of DME and water (4:1, 1.75 mL). To this, a 1,1'-[bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (13 mg, 0.018 mmol) was added, and the mixture was refluxed for 16 hours. After the mixture was cooled to room temperature, insoluble compounds were filtered and removed, and 4 mol/L hydrochloric acid was added to the filtrate. The precipitate was filtered and collected, and thus the title Compound 76 (35 mg, 48%) was obtained. 1H-NMR (DMSO-d6) δ: 12.27 (1H, s), 8.28-8.21 (2H, m), 8.16 (1H, dd, J=8.2, 1.6 Hz), 8.08 (1H, ddd, J=9.9, 2.2, 2.2 Hz), 8.06-7.98 (2H, m), 7.77 (1H, ddd, J=8.2, 8.2, 3.2 Hz), 7.58 (1H, dd, J=2.2, 1.6 Hz), 7.45 (1H, ddd, J=8.2, 8.2, 2.7 Hz). ESI-MS (m/z) 418 [M+H]+.
  • 8
  • [ 942070-38-4 ]
  • [ 1287793-22-9 ]
  • [ 1287793-66-1 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide; acetonitrile for 23h; Reflux; 118 Example 118 7-{5-(methoxycarbonyl)-1H-pyrrol-3-yl}-2-(3-fluorophenyl)-2H-[1,2,3]triazolo[4,5-f]quinoline-9-carboxylic acid (Compound 118) Compound 75 (120 mg, 0.35 mmol) obtained in Example 75, 1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)pyrrole-4-boronic acid pinacol ester (148 mg, 0.42 mmol), diisopropylethylamine (0.27 mL, 2.1 mmol), and a 1,1'-[bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (29 mg, 0.035 mmol) were suspended in a mixed solvent of acetonitrile and water (6:1, 3.5 mL), and the mixture was refluxed for 23 hours. After the mixture was cooled to room temperature, DMF was added thereto. Insoluble compounds were filtered and removed, and hydrochloric acid was added to the filtrate. The precipitate was filtered and collected, and thus the title Compound 118 (138 mg, 91%) was obtained. 1H-NMR (DMSO-d6) δ: 12.45 (1H, s), 8.28-8.22 (2H, m), 8.18-7.94 (4H, m), 7.76 (1H, ddd, J=8.3, 8.3, 6.3 Hz), 7.65 (1H, dd, J=2.1, 2.1 Hz), 7.45 (1H, ddd, J=8.8, 8.8, 2.5 Hz), 3.83 (3H, s). ESI-MS (m/z) 430 [M+H]+.
  • 9
  • [ 73183-34-3 ]
  • [ 294659-30-6 ]
  • [ 942070-38-4 ]
YieldReaction ConditionsOperation in experiment
79% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 80℃; for 0.333333h; Inert atmosphere; Microwave irradiation; Sealed tube;
76% Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether Inert atmosphere; Sonication; Stage #2: methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate at 80℃; for 0.333333h; Inert atmosphere; Microwave irradiation; 1 1 -tert-Butyl 2-methyl 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrrole- 1,2- dicarboxylate 4,4,4’,4’,5 ,5 ,5 ‘,5’-Octamethyl-2,2’-bi(1 ,3 ,2-dioxaborolane) (59.2 g, 233.08 mmol), (1,5- cyclooctadiene)(methoxy) iridium (I) dimer (1 .177 g, 1.78 mmol) and 4,4’-di-tert-butyl- 2,2’-bipyridine (0.953 g, 3.55 mmol) were placed in a 500 mL three-necked flask, which was purged with nitrogen. Degassed MTBE (500 mL) was added and the mixture was stirred and sonicated until a clear brown solution was obtained. 1-tert-butyl 2-methyl 1H-pyrrole-1,2-dicarboxylate (Sigma Aldrich) (50 g, 221.98 mmol) was added and flushed with nitrogen. The solution was heated in a microwave reactor at 80 °C for 20 minutes. The mixtures were combined and evaporated. The crude product was purified by flash silica chromatography, elution gradient 50 to 100% DCM in heptane to afford 1 -tert-butyl 2-methyl 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrrole- 1 ,2-dicarboxylate(59.3g, 76%) as a white crystalline solid.
68% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 65℃; for 2h; 1-tert-Butyl 2-Methyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate (1e)23 Bis(pinacolato)diboron (10.65 g, 41.96 mmol), (1,5-cyclooctadiene)(methoxy)iridium(I) dimer (0.424 g, 0.64 mmol) and 4,4′-di-tertbutyl-2,2′-bipyridine (BBBPY, 0.354 g, 1.32 mmol) were placed in a250 mL three-necked flask, which was purged with N2. Degassed tertbutylmethyl ether (MTBE) (100 mL) was added and the mixture wasstirred until a clear brown solution was obtained. 1-tert-Butyl 2-methyl 1H-pyrrole-1,2-dicarboxylate24 (9.00 g, 39.96 mmol) was addedand the mixture stirred at 65 °C for 2 h. The reaction was cooled toRT and concentrated in vacuo. The crude product was purified byflash silica gel chromatography with DCM as eluent. Fractions wereevaporated to afford a liquid. Heptane (60 mL) was added and thesolution was left stirring overnight. The resultant precipitate was filteredand washed with 5% DCM in heptane; yield: 9.60 g (68%); offwhitesolid (Lit.23 mp 133-135 °C).1H NMR (500 MHz, CDCl3): = 1.31 (s, 12 H), 1.58 (s, 9 H), 3.82 (s, 3H), 7.12 (d, J = 1.7 Hz, 1 H), 7.68 (d, J = 1.7 Hz, 1 H).MS (ES+): m/z = 297 ([M + H]+ - OtBu).
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 100℃; for 1h; Microwave irradiation;

  • 10
  • [ 942070-38-4 ]
  • [ 609-73-4 ]
  • [ 52635-93-5 ]
YieldReaction ConditionsOperation in experiment
692 mg Stage #1: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester; o-nitroiodobenzene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 1h; Stage #2: With N,N-dimethyl-formamide In water for 1h; Heating;
  • 11
  • [ 942070-38-4 ]
  • [ 1413063-63-4 ]
  • [ 1413064-08-0 ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere; 9.1 Step 1: Under N2, a mixture of acetic acid 2-bromo-6-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-benzyl ester (preparation described in intermediate-4, 300 mg, 0.699 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (270 mg, 0.769 mmol), Pd(dppf)Cl2 (171 mg, 0.21 mmol) and K2CO3 (289 mg, 2.19 mmol) in dioxane (15 mL) and water (3 mL) was heated at 100° C. for 4 h. The mixture was concentrated to dryness. The residue was purified by silica gel column chromatography (eluted with petroleum ether/ethyl acetate with a ratio of 2/1) to give 4-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (160 mg, yield 40%). LC-MS calcd for C32H35N3O7 (m/e) 573.25, obsd 473 [M-Boc+1]+.
  • 12
  • [ 156237-78-4 ]
  • [ 73183-34-3 ]
  • [ 942070-38-4 ]
YieldReaction ConditionsOperation in experiment
4.1 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; 1.3 Step 3: Preparation of 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-pyrrole-l,2- dicarboxylic acid 1-tert-butyl ester 2-methyl ester A mixture of 4-bromo-pyrrole-l,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (10 g, 33 mmol), bis(pinacolato)diboron (18 g, 66 mmol), KOAc (6.2 g, 66 mmol), Pd(dppf)Cl2 (1 g, 1.5 mmol) in 1,4-dioxane (150 mL) under nitrogen protection was stirred at 100 °C for 3 hours. The mixture was filtered through a Celite pad, and the filtrate was concentrated. The residue was purified by column chromatography to give 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- pyrrole-l,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (4.1 g) as a white solid.
180 g With bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Step 2: Preparation of compound M6 The compound M6-2 (100.000g) and pinacol diborate (167.000g) were dissolved in dioxane (500mL), potassium acetate (81.000g), (PPh3)2PdCl2 (5.000g) and Pd(dppf)2Cl2 (5.000g) were added, vacuum N2 replacement three times, the mixture was incubated at 100°C and reacted for 3hrs. After the reaction was completed, cooled down to below 50°C, desolvated, added petroleum ether (500mL), filtered, after desolventization, added petroleum ether (1000mL) again, stired for 45min, filtered. The filtrated was cooled to 0-5°C, there was solid precipitation , which was filtered and dried to obtain 180.000 g of compound. LC-MS [M+H]+=352.2.
  • 13
  • [ 942070-38-4 ]
  • 4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: zinc dibromide / acetonitrile / 4 h / 50 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Reflux; Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol / 3 h / Reflux; Inert atmosphere 4.1: sodium hydroxide; water / ethanol / 4 h / Reflux 5.1: sodium hydrogencarbonate; HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C 5.2: 2 h / 20 °C
  • 14
  • [ 942070-38-4 ]
  • 4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc dibromide / acetonitrile / 4 h / 50 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / Inert atmosphere; Reflux
  • 15
  • [ 942070-38-4 ]
  • 4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: zinc dibromide / acetonitrile / 4 h / 50 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / Inert atmosphere; Reflux 3: sodium hydroxide; water / ethanol / 1 h / 80 °C
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1-(tert-Butyl) 2-(4-chlorobenzyl) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.93

Chemical Structure| 1802005-04-4

[ 1802005-04-4 ]

1-tert-Butyl 2-ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.99

Chemical Structure| 1233525-93-3

[ 1233525-93-3 ]

2-Benzyl 1-(tert-butyl) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.96

Related Parent Nucleus of
[ 942070-38-4 ]

Pyrroles

Chemical Structure| 1802005-04-4

[ 1802005-04-4 ]

1-tert-Butyl 2-ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.99

Chemical Structure| N/A

[ N/A ]

1-tert-Butyl 2-(4-methoxybenzyl) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.91

Chemical Structure| 1351379-23-1

[ 1351379-23-1 ]

Methyl 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Similarity: 0.85

Chemical Structure| 1802005-04-4

[ 1802005-04-4 ]

1-tert-Butyl 2-ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.99

Chemical Structure| N/A

[ N/A ]

1-tert-Butyl 2-(4-methoxybenzyl) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Similarity: 0.91