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Product Details of [ 153435-68-8 ]

CAS No. :153435-68-8 MDL No. :MFCD01788369
Formula : C7H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :QHORMANADMCWSL-UHFFFAOYSA-N
M.W : 215.05 Pubchem ID :22049775
Synonyms :

Calculated chemistry of [ 153435-68-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.93
TPSA : 41.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.68
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.96
Solubility : 2.35 mg/ml ; 0.0109 mol/l
Class : Very soluble
Log S (Ali) : -1.28
Solubility : 11.2 mg/ml ; 0.052 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.27
Solubility : 0.115 mg/ml ; 0.000535 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

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 ]

* 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 [ 153435-68-8 ]

[ 153435-68-8 ] Synthesis Path-Downstream   1~23

  • 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.
  • 16
  • C36H55FN2O12 [ No CAS ]
  • [ 153435-68-8 ]
  • C43H61FN4O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 80℃; for 4h; Sonication; Inert atmosphere; 19 Example 19 0.75 g (1.09 mmol) of compound 6 was dissolved in 20 mL of acetonitrile (degassed by sonication)(Triphenylphosphine) palladium dichloride (38 mg, 0.054 mmol)Cuprous iodide 21 mg (0.11 mmol)Triethylamine 0.23 mL (1.64 mmol)And 0.82 g (3.82 mmol) of 3- (N-methyl) carbamoyl-5-bromopyridine.The reaction system was replaced with argon five times,Under argon protection,And stirred at 80 ° C for 4 h.After completion of the TLC monitoring reaction, distilled water (20 mL) was added to terminate the reaction,Extracted with ethyl acetate (40 mL)The upper organic phase was washed with saturated brine (20 mL)Steamed,Dry the solid. Column chromatography (100-200 mesh silica gel column,The mobile phase was V (dichloromethane): V (ethanol): V (aqueous ammonia = 10: 0.3: 0.1) to isolate 2'-O-acetyl-M. The 2'-O-acetyl-product M was dissolved in 20 mL of methanol, refluxed at 65 ° C for 3 h, the TLC was monitored and the reaction was complete,To give a dry product.The crude product M (65 mg, 0.079 mmol) was isolated by column chromatography (200-300 mesh silica gel column, mobile phase V (dichloromethane): V (ethanol): V (ammonia) = 10: 0.2: 0.1) ,The product M is 2-fluoro-3-O-dequelatinose-3-carbonyl-6-O-methylerythromycinA 9-O- [3- [5 '- (3' - (N-methyl) carbamoyl) pyridyl] -2-propynyl]12-cyclic carbonate,Yield 7.2%.
  • 17
  • [ 153435-68-8 ]
  • [ 74-88-4 ]
  • [ 292170-96-8 ]
YieldReaction ConditionsOperation in experiment
42 mg Sodium hydride (60% in oil) (28 mg) was added to a DMF (2.4 ml) solution containing 5-bromo-N-methylnicotinamide (100 mg), followed by stirring at 45C for 1 hour. Methyl iodide (43 mul) was added under ice cooling, followed by stirring at room temperature for 1 hour. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. Hexane was added to the obtained residue, solid matter was collected by filtration, and a white solid of 5-bromo-N,N-dimethylnicotinamide (42 mg) was thus obtained. 1H-NMR (DMSO-d6, 400MHz) delta:8.78 (d, 1H, J = 2.2Hz), 8.61 (d, 1H, J = 1.8Hz), 8.14 (dd, 1H, J = 1.9, 2.2Hz), 3.00 (s, 3H), 2.92 (s, 3H) MS (ESI, m/z): 229, 231 (M+H)
  • 18
  • 2'-O-acetyl-2-F-3-O-descladinosyl-3-keto-6-O-methylerythromycin A 9-O-propargyl oxime 11,12-cyclic carbonate [ No CAS ]
  • [ 153435-68-8 ]
  • 2-fluoro-3-O-descladinosyl-3-oxo-6-O-methylerythromycin A-9-O-[3-(3'-N-methylcarbomoylpyrid-5'-yl)-2-propargyl]oxime-11,12-cyclic carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.33% Stage #1: 2'-O-acetyl-2-F-3-O-descladinosyl-3-keto-6-O-methylerythromycin A 9-O-propargyl oxime 11,12-cyclic carbonate; 3-bromo-5-(N-methylcarbamoyl)pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile at 80℃; Inert atmosphere; Sealed tube; Alkaline conditions; Stage #2: In methanol at 60℃; for 1h; 4.5. General procedure for the synthesis of compounds 8 series General procedure: To a solution of CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq) and compound7 (1 eq) in MeCN (5 mL) were added ArBr (Ar a, b, c, e, f, g,h, k, l) or ArI (Ar q, r, s, t) (3 eq) and trimethylamine (1.5 eq). Thereaction mixture was flushed with argon and sealed in a pressuretube. The reaction mixture was stirred at 80 °C for 3-4 h. The reactionmixture was extracted with EtOAc, washed with water andbrine and concentrated in vacuo. The product was dissolved inMeOH (15 mL) at 60 °C for 1 h. The organic solvent was removed invacuum. The crude mixture was purified by column chromatographyon silica gel to give 8a, 8b, 8c, 8e, 8f, 8g, 8h, 8k, 8l, 8q, 8r, 8s,8t.To a solution of ArI (Ar = n, p) (3 eq) in MeCN (5 mL) was addedtrimethylamine (5 mL). The mixture was stirred at room temperaturefor 1 h, after which time CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq)and compound 7 (1 eq) were added. The reaction mixture wasflushed with argon and sealed in a pressure tube. The reactionmixture was stirred at 50 °C for 24 h. The reaction mixture wasextracted with EtOAc, washed with water and brine and concentratedin vacuum. The product was then dissolved in MeOH (15 mL)at 60 °C for 1 h. The organic solvent was removed in vacuo. Thecrude mixturewas purified by column chromatography on silica gelto give 8n and 8p.
  • 19
  • [ 97674-02-7 ]
  • [ 153435-68-8 ]
  • C9H10N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: tributyl(1-ethoxyvinyl)stannane; 3-bromo-5-(N-methylcarbamoyl)pyridine With bis-triphenylphosphine-palladium(II) chloride In toluene at 80℃; for 22h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In diethyl ether; water at 20℃; for 1h; PREPARATION OF INTERMEDIATE 125 Tributyl(l-ethoxyvinyl)tin (CAS 13965-03-02, 0.14 g, 0.19 mmol) followed by bis(triphenylphosphine)palladium(II) dichloride (CAS 13965-03-2, 0.1 eq, 0.138 g, (0645) 0.12 mmol) were added to a stirred solution of 5-bromo-A-mcthyl nicotinamide (CAS 153435-68-8, 0.42 g, 1.98 mmol) in toluene (10 mL) in a sealed tube and under N2. The mixture was stirred at 80 °C for 16 h. Then, more tributyl(l-ethoxyvinyl)tin (CAS 13965-03-02, 0.14 g, 0.19 mmol) and 6/.v(triphcnylphosphinc)palladium(ii) dichloride (CAS 13965-03-2, 0.1 eq, 0.138 g, 0.12 mmol) were added and stirred at 80 °C for 6 h. Then a 1M HC1 solution in diethyl ether (3.9 mL) was added and the mixture was stirred at rt for lh. The mixture was added to a stirred solution of sat NaHC03 and ice and extracted with DCM. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield intermediate 125 (105 mg, 30%) as a pale- yellow solid.
  • 20
  • [ 153435-68-8 ]
  • C21H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 22 h / 80 °C / Inert atmosphere; Sealed tube 1.2: 1 h / 20 °C 2.1: titanium(IV) isopropylate; sodium cyanoborohydride / tetrahydrofuran / 16 h / 70 °C
  • 22
  • tert‐butyl N‐(2‐cyano‐2‐methylideneethyl)‐N‐[2‐methoxy‐7‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)naphthalen‐1‐yl]carbamate [ No CAS ]
  • [ 153435-68-8 ]
  • tert-butyl N-(2-cyanoallyl)-N-[2-methoxy-7-[5-(methylcarbamoyl)-3-pyridyl]-1-naphthyl] carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; Cs2CO3 In 1,4-dioxane; water monomer at 100℃; for 0.5h; Microwave irradiation; 2 Preparation of tert-butyl N-(2-cyanoallyl)-N-[2-methoxy-7-[5-(methylcarbamoyl)-3-pyridyl]-1-naphthyl] carbamate To a solution of tert-butyl N-(2-cyanoallyl)-N-[2-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthyl]carbamate (60 mg, 129.21 μmol) in dioxane (2 mL) and water (0.4 mL) were added 5-bromo-N-methyl-pyridine-3-carboxamide (41.9 mg, 194.84 μmol), Cs2CO3 (0.125 g, 384.62 μmol), and PdCl2dppf (18 mg, 22.06 μmol). The reaction was heated at 100 °C for 30 min in a microwave. The reaction mixture was passed through a celite pad, and 2 mL of 0.5M EDTA was added. The resulting solution was stirred at r.t. for 40 min. The solution was washed with brine, dried over anhydrous sodium sulfate, 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 (60 mg, Yield 98%).
98% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; Cs2CO3 In 1,4-dioxane; water monomer at 100℃; for 0.5h; Microwave irradiation; 2 Preparation of tert-butyl N-(2-cyanoallyl)-N-[2-methoxy-7-[5-(methylcarbamoyl)-3-pyridyl]-1-naphthyl] carbamate To a solution of tert-butyl N-(2-cyanoallyl)-N-[2-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthyl]carbamate (60 mg, 129.21 μmol) in dioxane (2 mL) and water (0.4 mL) were added 5-bromo-N-methyl-pyridine-3-carboxamide (41.9 mg, 194.84 μmol), Cs2CO3 (0.125 g, 384.62 μmol), and PdCl2dppf (18 mg, 22.06 μmol). The reaction was heated at 100 °C for 30 min in a microwave. The reaction mixture was passed through a celite pad, and 2 mL of 0.5M EDTA was added. The resulting solution was stirred at r.t. for 40 min. The solution was washed with brine, dried over anhydrous sodium sulfate, 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 (60 mg, Yield 98%).
  • 23
  • tert‐butyl N‐(2‐cyano‐2‐methylideneethyl)‐N‐[2‐methoxy‐7‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)naphthalen‐1‐yl]carbamate [ No CAS ]
  • [ 153435-68-8 ]
  • 5-{8-[(2-cyano-2-methylideneethyl)amino]-7-methoxynaphthalen-2-yl}-N-methylpyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; Cs2CO3 / 1,4-dioxane; water monomer / 0.5 h / 100 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
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