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[ CAS No. 153435-68-8 ]

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Chemical Structure| 153435-68-8
Chemical Structure| 153435-68-8
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CAS No. :153435-68-8 MDL No. :MFCD01788369
Formula : C7H7BrN2O Boiling Point : 334.5±27.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :215.05 g/mol Pubchem ID :-
Synonyms :

Safety of [ 153435-68-8 ]

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

Application In Synthesis of [ 153435-68-8 ]

  • Downstream synthetic route of [ 153435-68-8 ]

[ 153435-68-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 20826-04-4 ]
  • [ 74-89-5 ]
  • [ 153435-68-8 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 5-bromo-3-pyridinecarboxylic acid With N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methylamine In N,N-dimethyl-formamide 2 Preparation of 5-bromo-N-methyl-pyridine-3-carboxamide A mixture of 5-bromopyridine-3-carboxylic acid (200 mg, 990.07 μmol), HATU (0.564 g, 1.48 mmol) and DIPEA (0.51 g, 3.95 mmol) in DMF (4 mL) was stirred at r.t. for 30 min. Methylamine (2 M, 0.99 mL, 1.98 mmol) was added. The resulting mixture was stirred at r.t. for 18h and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (3X). The combined organic phase was washed with saturated NaHCO3and brine, dried(MgSO4), filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 20-100% EtOAc/Hexane to afford the title compound (0.12 g, Yield 57%).
57% Stage #1: 5-bromo-3-pyridinecarboxylic acid With N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methylamine In N,N-dimethyl-formamide 2 Preparation of 5-bromo-N-methyl-pyridine-3-carboxamide A mixture of 5-bromopyridine-3-carboxylic acid (200 mg, 990.07 μmol), HATU (0.564 g, 1.48 mmol) and DIPEA (0.51 g, 3.95 mmol) in DMF (4 mL) was stirred at r.t. for 30 min. Methylamine (2 M, 0.99 mL, 1.98 mmol) was added. The resulting mixture was stirred at r.t. for 18h and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (3X). The combined organic phase was washed with saturated NaHCO3and brine, dried(MgSO4), filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 20-100% EtOAc/Hexane to afford the title compound (0.12 g, Yield 57%).
With thionyl chloride 1.) reflux, 2 h, 2.) CH2Cl2, RT, overnight; Yield given. Multistep reaction;
25.3 g Stage #1: 5-bromo-3-pyridinecarboxylic acid With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 0℃; for 5h; Reflux; Stage #2: methylamine In tetrahydrofuran 171.1 Step 1 Alternate route to prepare N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethyl-isoxazol-4-yl)-6-methoxy-9H-pyrido[3,4-b]indol-4-amine (Cpd. No. 323) Step 1: 5-Bromonicotinic acid (25 g, 124 mmol) was dissolved in 1,2-dichloroethane (200 mL). SOCl2 (27 mL, 371 mmol) was added at 0° C. followed by anhydrous DMF (0.2 mL) to initiate the reaction. The reaction mixture was heated at reflux for 5 h then concentrated on a rotatory evaporator. CH2Cl2 (100 mL) was added and removed on a rotatory evaporator and this process was repeated once. The remaining residues were dissolved in THF (100 mL) and methyl amine (124 mL, 2 M in THF) was added. Volatile components were removed on a rotatory evaporator and the remaining residues were dissolved in ethyl acetate followed by addition of water. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, then dried over anhydrous Na2SO4. The ethyl acetate was removed on a rotary evaporator affording ZYJ22 as a solid in 25.3 g. 1H NMR (300 MHz, DMSO-d6): 8.94 (d, J=1.73 Hz, 1H), 8.83 (d, J=2.17 Hz, 1H), 8.72 (br, 1H), 8.37 (t, J=1.93 Hz, 1H), 2.79 (s, 1.5H), 2.78 (s, 1.5H). ESI-MS calculated for C7H879BrN2O [M+H]+=214.98; Observed: 215.0.

  • 2
  • [ 36282-40-3 ]
  • [ 153435-68-8 ]
  • 5-bromo-4-(3-methoxyphenyl)-N-methyl-3-pyridinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide 1.) THF, 2 h, RT, 2.) THF, MeOH, 0 deg C, 2 h; Yield given. Multistep reaction;
  • 3
  • 1-(t-butoxycarbonyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-5-(tri-n-butylstannyl)-indole [ No CAS ]
  • [ 153435-68-8 ]
  • 1-(t-butoxycarbonyl)-5-(5-N-methylcarbamoyl-3-pyridyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-indol [ No CAS ]
YieldReaction ConditionsOperation in experiment
53 1-(t-butoxycarbonyl)-5-(5-N-methylcarbamoyl-3-pyridyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-indol STR175 PREPARATION 53 1-(t-butoxycarbonyl)-5-(5-N-methylcarbamoyl-3-pyridyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-indol STR175 1-(t-Butoxycarbonyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-5-(tri-n-butylstannyl)-indole (see Preparation 52) was reacted with 3-bromo-5-(N-methylcarbamoyl)pyridine in the presence of tri-o-tolylphosphine, triethylamine and palladium (II) acetate using a procedure similar to that described in Example 1. This yielded the title compound. Found: C,66.88; H,6.42; N,11.69; C26 H32 N4 O3.7/24CH2 Cl2 requires: C,66.71; H,6.94; N,11.84%.
  • 4
  • [ 20826-04-4 ]
  • [ 593-51-1 ]
  • [ 153435-68-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-bromo-3-pyridinecarboxylic acid; methylamine hydrochloride With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide 79 To a solution of 5.00 g of 5-bromonicotinic acid in 30 ml of DMF are added 1.99 g of methylamine hydrochloride, 3.31 g of 1-hydroxybenzotriazole, 9.54 g of 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride, and 8.04 ml of N-methylmorpholine. After stirring for 24 hours at ambient temperature, the mixture obtained is quenched with saturated aq. sodium hydrogen carbonate solution. After exhaustive extraction with EtOAc, the combined organic extracts obtained are dried and concentrated. 5-Bromo-N-methyl-nicotinamide is obtained.
  • 5
  • [ 153435-68-8 ]
  • 3-bromo-5-(1-methyl-1H-tetrazol-5-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-bromo-5-(N-methylcarbamoyl)pyridine With sodium azide In acetonitrile at 0℃; for 0.5h; Stage #2: With trifluoromethylsulfonic anhydride In acetonitrile at 20℃; for 25.5h; Stage #3: With sodium hydrogencarbonate In water; acetonitrile 79 To an ice-cold solution of 1.1 g of 5-bromo-N-methyl-nicotinamide in 50 ml of anhydrous ACN, 0.67 g of sodium azide are added. After stirring for 30 minutes, 0.86 ml of trifluoromethanesulfonic anhydride are added, the mixture obtained is stirred at ambient temperature for 60 minutes. Subsequently, 0.67 g of sodium azide are added. After 30 minutes, 2.58 ml of trifluoromethanesulfonic anhydride are added. The mixture obtained is stirred at ambient temperature for 24 hours and quenched with saturated aq. sodium hydrogen carbonate solution. After exhaustive extraction with EtOAc, the combined organic extracts obtained are dried and concentrated. 3-Bromo-5-(1 -methyl-1 H-tetrazol-5-yl)-pyridine is obtained.
YieldReaction ConditionsOperation in experiment
95% Stage #1: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: In N,N-dimethyl-formamide at 22℃; for 16h; 33.a a) 4-chloro-N,N-dimethylpyrimidine-2-carboxamide General procedure: 4-chloropyrimidine-2-carboxylic acid (600 mg, 3.78 mmol, Eq: 1), 2-(lH- benzo[d][l,2,3]triazol-1-yl)-l,l,3,3-tetramethylisouronium tetrafluoroborate (1.46 g, 4.54 mmol, Eq: 1.20) and N,N-diisopropylethylamine (2.5 g, 3.37 ml, 18.9 mmol, Eq: 5.00) were combined with dry dimethylformamide (10 ml). The reaction mixture was stirred at room temperature for 40 min, then dimethylamine hydrochloride (346 mg, 4.16 mmol, Eq: 1.10) was added. The reaction mixture was stirred at 22 °C for 16 h. The crude reaction mixture was concentrated in vacuo. The residue was diluted with saturated sodium bicarbonate and extracted with dichloromethane (x2). The combined organic layers were washed with brine, dried over sodium sulfate then filtered and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford the desired product as an orange oil (8 %). MS (m/z) = 186.1 [M + H]+.
  • 7
  • [ 153435-68-8 ]
  • N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-9H-pyrido[3,4-b]indol-4-amine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C 4.1: triethylamine; diphenyl phosphoryl azide / 33 h / 20 °C / Reflux 5.1: sodium hydride; copper(l) iodide / mineral oil; diethylene glycol dimethyl ether / 4 h / 120 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: boron tribromide / dichloromethane / 3 h / -78 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane / 1,4-dioxane; toluene / Reflux 8.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C 9.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux
  • 8
  • [ 153435-68-8 ]
  • C20H16BrNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C
  • 9
  • [ 153435-68-8 ]
  • C20H15Br2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C
  • 10
  • [ 153435-68-8 ]
  • C24H24Br2N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C 4.1: triethylamine; diphenyl phosphoryl azide / 33 h / 20 °C / Reflux
  • 11
  • [ 153435-68-8 ]
  • C19H15BrN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C 4.1: triethylamine; diphenyl phosphoryl azide / 33 h / 20 °C / Reflux 5.1: sodium hydride; copper(l) iodide / mineral oil; diethylene glycol dimethyl ether / 4 h / 120 °C / Inert atmosphere 5.2: 2 h / 20 °C
  • 12
  • [ 153435-68-8 ]
  • C12H9BrN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C 4.1: triethylamine; diphenyl phosphoryl azide / 33 h / 20 °C / Reflux 5.1: sodium hydride; copper(l) iodide / mineral oil; diethylene glycol dimethyl ether / 4 h / 120 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: boron tribromide / dichloromethane / 3 h / -78 °C
  • 13
  • [ 153435-68-8 ]
  • (x)C2HF3O2*C19H19N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C 4.1: triethylamine; diphenyl phosphoryl azide / 33 h / 20 °C / Reflux 5.1: sodium hydride; copper(l) iodide / mineral oil; diethylene glycol dimethyl ether / 4 h / 120 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: boron tribromide / dichloromethane / 3 h / -78 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane / 1,4-dioxane; toluene / Reflux
  • 14
  • [ 153435-68-8 ]
  • C20H18F3N5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: di-<i>tert</i>-butyl dicarbonate; dmap / tetrahydrofuran / 20 °C 3.1: acetic acid; pyridinium hydrobromide perbromide / water / 6 h / 75 °C 4.1: triethylamine; diphenyl phosphoryl azide / 33 h / 20 °C / Reflux 5.1: sodium hydride; copper(l) iodide / mineral oil; diethylene glycol dimethyl ether / 4 h / 120 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: boron tribromide / dichloromethane / 3 h / -78 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane / 1,4-dioxane; toluene / Reflux 8.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C
  • 15
  • [4-(benzyloxy)-3-methoxyphenyl]magnesium bromide [ No CAS ]
  • [ 153435-68-8 ]
  • C21H19BrN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.63 g Stage #1: [4-(benzyloxy)-3-methoxyphenyl]magnesium bromide; 3-bromo-5-(N-methylcarbamoyl)pyridine In tetrahydrofuran at 20℃; Stage #2: With N-chloro-succinimide In tetrahydrofuran; methanol at 20℃; 171.2 Step 2 Step 2: 1-(Benzyloxy)-4-bromo-2-methoxybenzene (30.5 g, 104 mmol) in anhydrous THF (100 mL) reacted with magnesium turning (3.0 g, 125 mmol) in the presence of catalytic iodine provided the corresponding Grignard reagents. The Grignard reagents was transferred into a THF solution of ZYJ22 (5.09 g, 49 mmol) and the reaction was stirred at ambient temperature for overnight. The reaction was then quenched with methanol (5.9 mL, 146 mmol) at 0° C. After 20 min, NCS (6.5 g, 49 mmol) was added in small portions. The reaction was stirred at ambient temperature for overnight and then quenched with 7% ammonia solution. Ethyl acetate was added to aqueous solution and the solid was collected affording the desired ZYJ23 (2.06 g). The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, then dried over anhydrous Na2SO4. The ethyl acetate was removed on a rotary evaporator and the remaining solid was mixed with diethyl ether. Filtration provided another portion of ZYJ23 in 4.57 g. 1H NMR (300 MHz, DMSO-d6): 8.85 (s, 1H), 8.51 (s, 1H), 8.34-8.22 (m, 1H), 7.54-7.30 (m, 5H), 7.12-7.08 (m, 1H), 6.89 (s, 1H), 6.82-6.72 (m, 1H), 5.10 (s, 2H), 3.72 (s, 3H), 2.52 (d, J=4.50 3H). ESI-MS calculated for C21H2079BrN2O3 [M+H]+=427.07; Observed: 427.17.
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