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CAS No. : | 1201186-54-0 | MDL No. : | MFCD12964053 |
Formula : | C13H10BrN3O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UMZKBENCNNDLRF-UHFFFAOYSA-N |
M.W : | 352.21 | Pubchem ID : | 52987643 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | To a solution of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (3.00 g, 11.1 mmol) in DMF (60 mL) at about 0 C. was added NaH (60% dispersion in mineral oil, 0.577 g, 14.4 mmol) in three portions. After about 15 min, p-toluenesulfonyl chloride (2.75 g, 14.4 mmol) was added and the reaction was allowed to warm slowly to ambient temperature. After about 16 h, the reaction mixture was poured onto ice-cold water (120 mL) and the precipitate was collected by vacuum filtration. The crude solid was dissolved in DCM (15 mL) and purified by silica gel chromatography eluting with DCM. The product-containing fractions were concentrated under reduced pressure to give 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (2.16 g, 52%): LC/MS (Table 2, Method d) Rt=1.58 min; MS m/z: 352/354 (M+H)+. | |
39.2% | To a 0 oc solution of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (1.22 g,4.52 mmol) in anhydrous DMF (10 mL) was added sodium hydride (253 mg, 6.33 mmol, 60 %).The mixture was stirred at 0 oc for 15 min, then paratoluensulfonyl chloride (865 mg, 4.51mmol) was added into the mixture. The resulting mixture was warmed to rt and stirred for 3 h.To the reaction mixture was added ice-water (40 mL) to quench the reaction, and the resultingmixture was extracted with ethyl acetate (30 mL x 3). The combined organic layers were washedwith saturated brine (60 mL), dried over anhydrous sodium sulfate and filtered. The filtrate wasconcentrated in vacuo and the residue was purified by silica gel column chromatography(PE/EtOAc (v/v) = 1011) to give the title compound as a yellow solid (624 mg, 39.2 %). | |
39.2% | 5-Bromo-3-(2-trimethylsilylacetylene)pyrazine-2-amine (1.22 g, 4.52 mmol)Dissolved in anhydrous DMF (10 mL), cooled to 0 C,Add sodium hydride (253 mg, 6.33 mmol, 60%),The resulting mixture was stirred at 0 C for 15 minutes and then p-toluenesulfonyl chloride ( 865 mg, 4.51 mmol).The resulting mixture was warmed to room temperature and the reaction was continued for 3 hours.It was quenched with ice water (40 mL) andEtOAc.The separated organic phase was washed with brine (60 mL).Dry over anhydrous sodium sulfate and concentrate the filtrate under reduced pressure.The residue obtained was purified by silica gel column chromatography(PE/EtOAc (nu/nu)=10/1),The title compound was obtained as a yellow solid (624mg, 39.2%). |
30.7% | The compound 2-amino-3-(trimethylsilylethynyl)-5-bromopyrazin 5a (5.0g, 18.5mmol) was dissolved in DMF (100ml), at 0 C added portionwise NaH (0.96g, 24 mmol), stirred for 2 hours, TsCl (4.6 g, 24 mmol) was added portionwise.After stirring at room temperature for 10 h, TLC showed the reaction was completed. 0 C about 100ml was added an aqueous solution of ammonium chloride, the aqueous phase was extracted three times with ethyl acetate (100 mL), the organic phases were combined,Once, dried over anhydrous sodium sulfate washed with brine, and dried to give the crude product under reduced pressure using a rotary evaporator,Through the column to give the title compound 5b (2.0g, 5.6mmol), a yield of 30.7% | |
2.16 g | Step B: 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine to 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine [0184] To a solution of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (3.00 g, 11.1 mmol) in DMF (60 mL) at about 0 C. is added NaH (60% dispersion in mineral oil, 0.577 g, 14.4 mmol) in three portions. After about 15 min, p-toluenesulfonyl chloride (2.75 g, 14.4 mmol) is added and the reaction is allowed to warm slowly to ambient temperature. After about 16 h, the reaction mixture is poured onto ice-cold water (120 mL) and the precipitate is collected by vacuum filtration. The crude solid is dissolved in DCM (15 mL) and purified by silica gel chromatography eluting with DCM to give 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (2.16 g, 52%): LC/MS (Table 1, Method c) Rt=1.58 min; MS m/z: 352, 354 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | A solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (78.0 g, 394 mmol, Ark Pharm) in anhydrous DMF (272 mL) was added drop-wise over about 60 min to a stirred suspension of NaH (12.8 g, 532 mmol) in anhydrous DMF (543 mL) at about 0-5 C. The brown reaction solution was stirred for about 30 min at about 0-5 C. then a solution of p-toluenesulfonyl chloride (94.0 g, 492 mmol) in anhydrous DMF (272 mL) was added drop-wise over about 60 min at about 0-5 C. The reaction mixture was stirred at about 0-5 C. for about 1 h then allowed to warm to ambient temperature and stirred for about 18 h at ambient temperature. The reaction mixture was poured slowly into ice water (6 L), followed by the addition of aqueous 2.5 N NaOH (50.0 mL, 125 mmol). The precipitate was collected by filtration and stirred with cold water (3×200 mL). The solid was collected by filtration and dried to constant weight in a vacuum oven at about 55 C. to yield 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (134.6 g, 97%) as a pale beige solid: LC/MS (Table 2, Method d) Rt=1.58 min; MS m/z: 352/354 (M+H)+. | |
86% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 30℃; for 8h;Inert atmosphere; | Under the protection of nitrogen content 60% of NaH 12 mmol suspended in DMF 30 ml in, adding dissolved in 10 ml DMF of the B - 110 37.4 mmol, reaction 1 h after, adding dissolved in 20 ml DMF to toluene sulfonyl chloride 12 mmol, 30 C reaction 8 h after, the reaction mixture of ethyl acetate extraction 2 time, the combined ethyl acetate after drying, after recovering ethyl acetate, petroleum ether ethyl acetate column chromatography (5:1), the obtained product is 3.0 g, yield 86% |
79.3% | With sodium hydride; In tetrahydrofuran; mineral oil; at -15 - 20℃; for 1h; | 2-bromo-5H-pyrrolo [2,3-b] pyrazine (10 g, 50.5 mmol)Of tetrahydrofuran (150 mL)Was added sodium hydride (60%, 3.1 g, 78 mmol)The mixture was stirred at room temperature for 1 hour,P-toluenesulfonyl chloride (12.6 g, 65.4 mmol) was added under ice-Continue to stir at room temperature,Diluted with water (100 mL)Dichloromethane extraction (100 mL x 3),Dried over anhydrous sodium sulfate,Concentrated column chromatography (petroleum ether / ethyl acetate (v / v) = 8/1)To give 14.1 g of a pale yellow flocculent solid in a yield of 79.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With racemic-2-(di-tert-butylphosphino)-1,1?-binaphthyl; zinc;palladium(II) trifluoroacetate; In ISOPROPYLAMIDE; at 50 - 95℃;Inert atmosphere; | A 5-L reactor was charged with <strong>[1201186-54-0]2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine</strong> (98.8 g, 281 mmol, Preparation No.7), zinc dust (3.50 g, 53.3 mmol), palladium (II) trifluoroacetate (4.0 g, 12 mmol), and racemic-2-(di-t-butylphosphino)-1,1'-binapthyl (9.8 g, 24.7 mmol). The flask was equipped with a powder addition device into which zinc cyanide (10.0 g, 157 mmol) was placed to be added at a later step. The vessel was purged with argon for no longer than about 30 min and then argon sparged DMA (2 L) was added to the reactor. The mixture was stirred and heated to about 50 C. while maintaining an argon sparge. The resulting dark brown solution was further heated to about 95 C. while adding the zinc cyanide, from the powder addition device, portion-wise over about 15 min. Upon reaching about 95 C., the brown mixture is stirred for about an additional 16 h. The reaction mixture was cooled to room temperature, resulting in the precipitation of salts. The mixture was filtered through a Buchner funnel containing filter-aid and the filter cake was washed with DMA (20 mL). A solution of the crude product in DMA was added to cold (<10 C.) water (16 L) and stirred for about 30 min. The resulting suspension was filtered and the filter cake was rinsed again with water (1 L). The resulting wet cake was dried in a vacuum oven at about 50 C. The crude solid was dissolved in DCM (1.5 L) and further dried over anhydrous MgSO4. After filtration, the solution was passed through a pad of silica (140 g), washing with additional solvent until only predominantly impurities were detected eluting off the pad. The solvent was removed and the crude solid was triturated with MeOH/DCM (4:1, 10 volumes of solvent per gram of crude solid) at ambient temperature for about 5 h. The solid was filtered and washed with MeOH (300 mL). The product was dried in a vacuum oven to provide 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbonitrile (58.8 g, 70%) as a colorless solid: 1H NMR (400 MHz, CDCl3) delta 8.67 (s, 1H), 8.21 (d, J=4.2 Hz, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.1 Hz, 2H), 6.89 (d, J=4.2 Hz, 1H), 2.42 (s, 3H). A 2-L 316-stainless steel pressure reactor was charged with 5% Pd/C (15.4 g of 63.6 wt % water wet material, 5.6 g dry basis, Johnson Matthey A503032-5), 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbonitrile (55 g, 184 mmol), THF (1.1 L), deionized water (165 mL), aqueous HCl, (37 wt %, 30 mL, 369 mmol) and quinoline (1.1 mL, 9.0 mmol). The vessel was purged, pressurized, and maintained at 40 psi with hydrogen supplied from a high pressure reservoir. The mixture was vigorously agitated at about 25 C. After about 5 h the reactor was vented and purged with nitrogen to remove most of the dissolved hydrogen, and the reaction mixture was filtered to remove the catalyst. The reactor and catalyst cake were rinsed with THF:H2O (1:1, 2×40 mL). The combined filtrate and rinses were concentrated and EtOH (500 mL) was added. After two additional solvent switches with EtOH (2×500 mL), the crude residue was concentrated to give a residue (76 g) that was suspended in EtOH (550 mL) and stirred at ambient temperature for about 4 h. The solid was collected by filtration and washed with cold EtOH (50 mL). The wet cake was dried in a vacuum oven to provide (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride (51.2 g, 82%) as a colorless solid: LC/MS (Table 2, Method a) Rt=1.44 min; MS m/z: 303 (M+H)+. |
58.8% | With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; | The compound <strong>[1201186-54-0]2-bromo-5-p-toluenesulfonyl-5H-pyrrolo[2,3-b]pyrazine</strong> 5b (4.0 g, 11.3 mmol), Zinc cyanide (2.4 g, 22.7 mmol) and Pd(PPh3)4 (1.6 g) were dissolved in DMF (100 ml) and reacted at 110 C overnight under nitrogen. TLC showed completion of the reaction, 150ml of ice water was added, extracted with ethyl acetate (100 mL) the aqueous phase twice, the organic phases are combined, once, dried over anhydrous sodium sulfate washed with brine, and dried to give the crude product under reduced pressure using a rotary evaporator, through the column to give the title compound 5c (2.0g, 6.7mmol), a yield of 58.8% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a flask was added Pd2(dba)3 (3.90 g, 4.26 mmol), di-tert-butyl-(2',4',6'-triisopropylbiphenyl-2-yl)phosphane (3.62 g, 8.52 mmol), and anhydrous 1,4-dioxane (453 mL). The catalyst-ligand mixture was degassed via vacuum/nitrogen purge (3 times) and heated at about 80 C. for about 10 min. The reaction mixture is briefly removed from the oil bath then <strong>[1201186-54-0]2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine</strong> (30.0 g, 85 mmol, Preparation No.7), tert-butyl hydrazinecarboxylate (16.9 g, 128 mmol), and NaOt-Bu (12.28 g, 128 mmol) were added. After an additional vacuum/nitrogen purge, the reaction was heated at about 80 C. After about 50 min, the reaction mixture was cooled to ambient temperature and filtered through a pad of silica gel (6 cm in height×6 cm in diameter), topped with Celite (1 cm in height×6 cm in diameter), while washing with EtOAc (3×150 mL). Water (300 mL) was added to the filtrate and the organic layer was separated. The aqueous layer was extracted with additional EtOAc (3×200 mL). The combined organic extracts were washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine (400 mL each), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give a dark brown oil (45 g). The brown oil was dissolved in DCM (250 mL), silica gel (200 g) was added, and the mixture was concentrated under reduced pressure. The resulting silica mixture was purified using silica gel chromatography eluting with a gradient of 25-65% EtOAc in heptane to give a mixture of tert-butyl 2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate [major regioisomer] and tert-butyl 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate [minor regioisomer] (18.8 g, 50%): LC/MS (Table 2, Method d) Rt=1.47 min; MS m/z: 404 (M+H)+.; To a mixture of tert-butyl 2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate and tert-butyl 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate (18.8 g, 46.6 mmol, Preparation No.8) in 1,4-dioxane (239 mL) was added HCl (4 M in 1,4-dioxane, 86 mL, 345 mmol). The reaction was heated at about 60 C. for about 1 h and then cooled to about 15-20 C. The solid was collected by vacuum filtration, washed with cold 1,4-dioxane (2×20 mL), and then stirred with a solution of saturated NaHCO3 and water (1:1, 150 mL). After about 1 h, the effervescence had subsided and the solid was collected by vacuum filtration, washed with ice cold water (3×20 mL), and dried in a vacuum oven to a constant weight to afford 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine as a light yellowish brown solid (8.01 g, 50%): LC/MS (Table 2, Method d) Rt=1.28 min; MS m/z: 304 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate; tert-butyl XPhos;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 80℃; for 0.833333h; | To a flask was added Pd2(dba)3 (3.90 g, 4.26 mmol), di-tert-butyl-(2',4',6'-triisopropylbiphenyl-2-yl)phosphane (3.62 g, 8.52 mmol), and anhydrous 1,4-dioxane (453 mL). The catalyst-ligand mixture was degassed via vacuum/nitrogen purge (3 times) and heated at about 80 C. for about 10 min. The reaction mixture is briefly removed from the oil bath then <strong>[1201186-54-0]2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine</strong> (30.0 g, 85 mmol, Preparation No.7), tert-butyl hydrazinecarboxylate (16.9 g, 128 mmol), and NaOt-Bu (12.28 g, 128 mmol) were added. After an additional vacuum/nitrogen purge, the reaction was heated at about 80 C. After about 50 min, the reaction mixture was cooled to ambient temperature and filtered through a pad of silica gel (6 cm in height×6 cm in diameter), topped with Celite (1 cm in height×6 cm in diameter), while washing with EtOAc (3×150 mL). Water (300 mL) was added to the filtrate and the organic layer was separated. The aqueous layer was extracted with additional EtOAc (3×200 mL). The combined organic extracts were washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine (400 mL each), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give a dark brown oil (45 g). The brown oil was dissolved in DCM (250 mL), silica gel (200 g) was added, and the mixture was concentrated under reduced pressure. The resulting silica mixture was purified using silica gel chromatography eluting with a gradient of 25-65% EtOAc in heptane to give a mixture of tert-butyl 2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate [major regioisomer] and tert-butyl 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate [minor regioisomer] (18.8 g, 50%): LC/MS (Table 2, Method d) Rt=1.47 min; MS m/z: 404 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 2.5h; | To a solution of <strong>[1201186-54-0]2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine</strong> (624 mg, 1.77 mmol) in1,4-dioxane (10 mL) were added tert-butyl carbamate (311 mg, 2.65 mmol), potassium carbonate(734 mg, 5.31 mmol), xantphos (209 mg, 0.35 mmol) and palladium acetate (41 mg, 0.17 mmol).The mixture was heated to 105 oc and stirred for 2.5 h. The reaction mixture was concentrated invacuo and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1011)to give the title compound as a white solid (513 mg, 75 %). |
75% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 2.5h;Inert atmosphere; | 2-Bromo-5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazine (624 mg, 1.77 mmol) was dissolved in 1,4-dioxane (10 mL).Add tert-butyl carbamic acid (311 mg, 2.65 mmol), potassium carbonate (734 mg, 5 · 31 mmol),Xantphos (209mg, 0.35mmol)And palladium acetate 41 mg, 0.17 mmol), and the resulting mixture was heated to 105 C under a nitrogen atmosphere and stirred for 2.5 hours.The reaction solution was concentrated under reduced pressure.The residue obtained was subjected to silica gel column chromatography(PE/EtOAc (nu/nu) =10/1) purified,The title compound was obtained as a white solid (513 mg, 75%). |
71% | With C36H26OP2*Pd(2+)*2C2H3O2(1-); caesium carbonate; In 1,4-dioxane; at 100℃; for 15h;Inert atmosphere; | Under the protection of nitrogen will be 10 mmol B - 2 dissolved in 30 ml dioxane, adding Cs2CO315 Mmol, adding catalyst Xanphos - Pd (OAc)2Complex 0.3 mmol, tert-butyl carbamate 15 mmol, 100 C reaction 15 h after, the reaction mixture of ethyl acetate extraction 2 time, the combined ethyl acetate after drying, after recovering ethyl acetate, petroleum ether ethyl acetate crystallization (5:1), the obtained product is 2.74 g, yield 71%, |
With pyridine; at 50℃; for 2h; | (6) The compound 5 was dissolved in pyridine, and then the t-butyl carbamate was slowly added thereto, and the mixture was reacted at 50 C for 2 hours. After the reaction was completed, the mixture was extracted twice with aqueous sodium carbonate solution and dried over sodium sulfate. , (tert-butyl 5-toluenesulfonyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate was obtained. |
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