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Chemical Structure| 235426-31-0 Chemical Structure| 235426-31-0

Structure of 235426-31-0

Chemical Structure| 235426-31-0

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Product Details of [ 235426-31-0 ]

CAS No. :235426-31-0
Formula : C5H7BrN2
M.W : 175.03
SMILES Code : CC1=CN=C(Br)N1C
MDL No. :MFCD06659902
Boiling Point : No data available

Safety of [ 235426-31-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of [ 235426-31-0 ]

* 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 [ 235426-31-0 ]

[ 235426-31-0 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 10447-93-5 ]
  • [ 235426-31-0 ]
  • 2
  • [ 1128191-83-2 ]
  • [ 235426-31-0 ]
  • [ 1128191-66-1 ]
YieldReaction ConditionsOperation in experiment
38% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 0.666667h;Microwave irradiation; 57B. N-[3-(l,5-dimethylimidazol-2-yl)-4-methyl-phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3- carboxamide; In a 10 mL vial was placed 2-methyl-N-(4-methyl-3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-6-(trifluoromethyl)nicotinamide (0.1 g, 0.24 mmol), CS2CO3 (0.194 g, 0.59 mmol), and 2-bromo- 1,5 -dimethyl- lH-imidazole (0.062 g, 0.36 mmol) in dioxane (4 mL) to give a colorless suspension. The reaction mixture was diluted with water (1 mL). Nitrogen was bubbled through the mixture for 20 min before Pd(PPh3 )4 (0.041 g, 0.04 mmol) was added and the reaction was heated to 100 0C using a microwave for 40 min. After concentration in vacuo, the residue was diluted with EtOAc (10 mL) and water (10 mL). The aqueous layer was extracted with EtOAc (2 X 10 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give the crude product that was purified by ISCO MPLC (10% MeOH in DCM) to give the title compound (0.035 g, 38% yield). 1H NMR (DMSO-d6) delta 2.13 (s, 3 H), 2.23 (s, 3 H), 2.64 (s, 3 H), 3.34 (s, 3 H), 6.76 (s, 1 H), 7.33 (s, 1 H), 7.65 (s, 2 H), 7.89 (s, IH), 8.18 (s, 1 H), 10.63 (s, 1 H). MS (M+H+) = 389.
  • 3
  • [ 958646-69-0 ]
  • [ 235426-31-0 ]
  • [ 1128191-82-1 ]
YieldReaction ConditionsOperation in experiment
50% With potassium acetate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 1.41667h;Microwave irradiation; Example 12N-[4-chloro-3-(l,5-dimethylimidazol-2-yl)phenyl]-2-methoxy-pyridine-3-carboxamide12A. 4-Chloro-3-(l,5-dimethylimidazol-2-yl)aniline; In a 35 mL vial was placed 5-amino-2-chlorophenylboronic acid (0.7 g, 4.08 mmol), 2- bromo-l,5-dimethyl-lH-imidazole (1.072 g, 6.13 mmol), and KOAc (1.203 g, 12.25 mmol) in dioxane (8 mL) to give a yellow suspension. The reaction mixture was diluted with water (2.0 mL) and after bubbling in nitrogen for 10 min, Pd(PPlIs)4 (0.472 g, 0.41 mmol) was added. The reaction was heated using a microwave at 100 0C for 85 min. After concentration in vacuo, the residue was purified by ISCO MPLC (10% MeOH in DCM) to give the product (0.45 g, 50% yield). 1H NMR (DMSO-d6) delta 2.19 (s, 3 H), 3.30 (s, 3 H), 5.41 (s, 2 H), 6.56 (d, 1 H), 6.66 (m, 2 H), 7.16 (d, 1 H). MS (M+H+) = 222.
  • 4
  • [ 1128191-78-5 ]
  • [ 235426-31-0 ]
  • [ 1128191-07-0 ]
YieldReaction ConditionsOperation in experiment
18% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 0.333333h;Microwave irradiation; 1C. N- [4-chloro-3-(l ,5-dimethylimidazol-2-yl)phenyl] -2-methyl-6-(trifluoromethyl)pyridine-3- carboxamide; In a 20 mL tube was added boronic acid (0.12 g, 0.33 mumol), Cs2CO3 (0.22 g, 0.67mumol), 2-bromo-l,5-dimethyl-lH-imidazole (0.12 g, 0.67mumol) in dioxane (8 mL) and water (2 mL) to give a suspension. Nitrogen was bubbled into the tube for about 15 min before Pd(PPh3 )4 (0.039 g, 0.03 mumol) was added. The reaction mixture was heated in microwave oven for 20 min at 100 0C. The reaction was concentrated in vacuo and then 1 mL of DMSO was added to dissolve the residue. After filtration, the crude sample was purified by Gilson etaPLC to give the title compound (24.7 mg, 18%). 1H NMR (DMSO-d6) delta 2.24 (s, 3 H), 2.64 (s, 3 H), 3.38 (s, 3 H), 6.84 (s, 1 H), 7.63 (s, 1 H), 7.82 (s, 1 H), 7.90 (s, 2 H), 8.21 (s, 1 H), 10.89 (s, 1 H). MS (M+H+) = 409.
  • 5
  • [ 1126369-28-5 ]
  • [ 235426-31-0 ]
  • [ 1126365-64-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 150.0℃; for 0.666667h;Inert atmosphere; Microwave irradiation; General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.
  • 6
  • [ 235426-31-0 ]
  • [ 375853-82-0 ]
  • tert-butyl 4-(1,5-dimethyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 100.0℃; for 5h;Inert atmosphere; tert-Butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1 (2H)-carboxylate (2.0 g, 6.55 mmol), 2-bromo-1,5-dimethyl-IH-imidazole (1.13 g, 6.45 mmol) and CsF (2.9 g,1.85 mmol) were dissolved in DME: MeCH (2:1, 30 mL). The reaction mixture was degassed for 5 mins, then Pd(PPh3)4 (73 mg, 0.064 mmol) was added and the resulting reaction mixture was stirred for 5 h at 100C. The reaction mixture was partitioned between H20 (100 mL) andEtOAc (100 mL), the aqueous layer was further extracted with EtOAc (2 x 100 mL), the organic layers were combined, dried (Na2SO4) and the solvents were removed in vacuo. The residue was purified by column chromatography (normal silica, mesh size: 60-120, 13% to 17% Ethyl acetate in Hexane) to give tert-butyl 4-(1 ,5-dimethyl-1 H-imidazol-2-yl)-3,6-dihydropyridine- 1(2H)-carboxylate (1 g, 55%) as a yellow gum.LCMS (Method F): m/z 278 (M+H) (ES), at 1.70 mm, UV active
  • 7
  • [ 461699-81-0 ]
  • [ 235426-31-0 ]
  • 4-(1,5-dimethyl-1H-imidazol-2-yl)-2-methoxyaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 100.0℃; for 18h;Microwave irradiation; General procedure: Preparation 45 (1126) -methoxy-4-(1 -methyl-1 -/-pyrazol-3-yl)aniline (1127) (1128) To a solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (310 mg, 1 .244 mmol) and 3-bromo-1 -methyl-1 -/-pyrazole (154 mg, 0.957 mmol) in THF (3 ml_) was added Pd(dppf)Cl2-DCM (40 mg, 0.049 mmol) and 2M aqueous Na2CC>3 (1 ml_) and the reaction was heated to 65 C for 18 hours. The reaction was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, the combined organic layers were washed with water and brine, dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-60% EtOAc in cyclohexane to afford the title compound (34 mg, 18%). (1129) 1 H NMR (500 MHz, CDCI3): delta ppm 7.33 (d, J = 18.8 Hz, 2H), 7.28 (d, J = 1 .2 Hz, 2H), 7.20 (d, J = 7.9 Hz, 1 H), 6.74 (dd, J = 7.9, 1 .2 Hz, 1 H), 6.45 (dd, J = 2.2, 1 .2 Hz, 1 H), 3.95 (m, 6H), 3.85 (br s, 2H). (1130) HRMS (ESI) MS m/z calcd for C11 H14N3O [M+H]+ 204.1 131 , found 204.1 141 .
  • 8
  • [ 121505-93-9 ]
  • [ 235426-31-0 ]
  • C12H19N3O3 [ No CAS ]
  • 9
  • [ 235426-31-0 ]
  • C13H21N5O2 [ No CAS ]
  • 10
  • [ 235426-31-0 ]
  • C14H21N5O4 [ No CAS ]
  • 11
  • [ 235426-31-0 ]
  • (+/-)-tert-butyl 5-[[bis(tert-butoxycarbonyl)amino]methyl]-5-(1,5-dimethylimidazol-2-yl)-2,4-dioxo-imidazolidine-1-carboxylate [ No CAS ]
  • 12
  • [ 23328-88-3 ]
  • [ 333-27-7 ]
  • [ 235426-31-0 ]
  • 13
  • N-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-methylmethanesulfonamide [ No CAS ]
  • [ 235426-31-0 ]
  • C13H18N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
23.78% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 110.0℃; for 24h; A mixture of <strong>[235426-31-0]2-bromo-1,5-dimethyl-1H-imidazole</strong> (1 .Og, 5.71 mmol, 1. Oeq) and N-(2-amino-5-(4,4,5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2- yl)phenyl)-N-methylmethaneSulfonamide (2.04g, 6.28mmol, 1.leq) in 1,4-dioxane (lOmL) wasdegassed with argon for 10 mm followed by addition of [1,1?-Bi s(diphenylphosphino)ferrocene]palladium(II) dichloride(0 .208g, 0. 28mmol, 0.05 eq) and potassium carbonate(0.236g, 1.7lmmol, 3.Oeq). Reaction mixture was stirred at 110c for 24h. Upon completion, reaction mixture was transferred into cold water and extracted with ethyl acetate. Organic layer combined, dried over Na2SO4 and concentrated in vacuo to obtain crude product. This was purified by column chromatography and compound was eluted in 15% ethyl acetate in hexane as eluant to obtain pure 169.1 (0.4g, 23.78 %). MS(ES): m/z 296.37 [M+H]t
 

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