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[ CAS No. 85553-53-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 85553-53-3
Chemical Structure| 85553-53-3
Chemical Structure| 85553-53-3
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Product Details of [ 85553-53-3 ]

CAS No. :85553-53-3 MDL No. :MFCD02684103
Formula : C12H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :SAPNGHSAYQXRPG-UHFFFAOYSA-N
M.W : 183.21 Pubchem ID :3710039
Synonyms :

Calculated chemistry of [ 85553-53-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.06
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 2.56
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 2.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.294 mg/ml ; 0.0016 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.82 mg/ml ; 0.00448 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.49
Solubility : 0.00593 mg/ml ; 0.0000324 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 85553-53-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85553-53-3 ]

* 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 [ 85553-53-3 ]

[ 85553-53-3 ] Synthesis Path-Downstream   1~67

  • 1
  • [ 867-13-0 ]
  • [ 85553-53-3 ]
  • (E)-3-(3-Pyridin-2-yl-phenyl)-acrylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) THF, 2.) THF, RT, 30 min; Yield given. Multistep reaction;
  • 2
  • 2-(3-[1,3]Dioxolan-2-yl-phenyl)-pyridine [ No CAS ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In toluene for 0.166667h;
  • 3
  • [ 109-04-6 ]
  • [ 87199-16-4 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
92% With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate In methanol; water; toluene for 18h;
91% With potassium carbonate In N,N-dimethyl acetamide; water at 100℃; for 2h;
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide; toluene for 18h; Heating;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; toluene for 36h; Reflux; Inert atmosphere;
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane at 100℃; Inert atmosphere;
With Palladium catalyst
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃;

  • 4
  • [ 85553-53-3 ]
  • [ 263349-10-6 ]
  • 3-[(3-phenoxyphenyl)[[3-(2-pyridinyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;
  • 5
  • [ 109-04-6 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Mg, 2.) (Ph3P)2NiCl2 / 2.) Et2O, 3 d 2: 1N HCl / toluene / 0.17 h
With caesium carbonate In tetrahydrofuran at 65℃; for 3h; 118.A A mixture of 3-formyl boronic acid (Lancaster, 5.0 g, 33 mmol), 2-bromopyridine (Aldrich, 4.80 mL, 501 mmol), Cs2CO3 (37.6 g, 115 mmol) and PdCl2(PPh3)2 (1.02 g, 1.5 mmol) in 90 mL THF was heated to 65° C. After 3 h the reaction was cooled to RT and partitioned between EtOAc/H2O. The aqueous layer was extracted with EtOAc (3*) and the combined organics were washed with brine and dried over Na2SO4. The solution was filtered, evaporated onto SiO2 and purified by flash column chromatography with EtOAc/hexane (0:1→1:4) as eluant to give the title compound as a light yellow oil. MS m/z 184 (MH)+.
  • 6
  • [ 17789-14-9 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Mg, 2.) (Ph3P)2NiCl2 / 2.) Et2O, 3 d 2: 1N HCl / toluene / 0.17 h
  • 7
  • [ 85553-53-3 ]
  • [ 158503-43-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C 3: (COCl)2, DMSO, NEt3
  • 8
  • [ 85553-53-3 ]
  • (E)-3-(3-Pyridin-2-yl-phenyl)-prop-2-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C
  • 9
  • [ 85553-53-3 ]
  • (3S,4S)-3-Hydroxymethyl-4-[2-(3-pyridin-2-yl-phenyl)-ethyl]-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C 3: (COCl)2, DMSO, NEt3 4: LiN(TMS)2 5: NEt3 6: H2 / 5percent Pd/C / ethanol / 24 h / Ambient temperature 7: p-TsCl, pyridine 8: CF3COOH, n-BuOH
  • 10
  • [ 85553-53-3 ]
  • (E)-3-Hydroxy-2-hydroxymethyl-5-(3-pyridin-2-yl-phenyl)-pent-4-enoic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C 3: (COCl)2, DMSO, NEt3 4: LiN(TMS)2
  • 11
  • [ 85553-53-3 ]
  • (3S,4S)-4-[2-(3-Pyridin-2-yl-phenyl)-ethyl]-3-trityloxymethyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C 3: (COCl)2, DMSO, NEt3 4: LiN(TMS)2 5: NEt3 6: H2 / 5percent Pd/C / ethanol / 24 h / Ambient temperature 7: p-TsCl, pyridine
  • 12
  • [ 85553-53-3 ]
  • (2S,3S)-3-Hydroxy-5-(3-pyridin-2-yl-phenyl)-2-trityloxymethyl-pentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C 3: (COCl)2, DMSO, NEt3 4: LiN(TMS)2 5: NEt3 6: H2 / 5percent Pd/C / ethanol / 24 h / Ambient temperature
  • 13
  • [ 85553-53-3 ]
  • (E)-(2S,3S)-3-Hydroxy-5-(3-pyridin-2-yl-phenyl)-2-trityloxymethyl-pent-4-enoic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) NaH / 1.) THF, 2.) THF, RT, 30 min 2: DIBAL-H / tetrahydrofuran; hexane / 1 h / -20 °C 3: (COCl)2, DMSO, NEt3 4: LiN(TMS)2 5: NEt3
  • 14
  • [ 75-52-5 ]
  • [ 85553-53-3 ]
  • [ 881208-08-8 ]
YieldReaction ConditionsOperation in experiment
72.5% With ammonium acetate at 90℃; for 4h;
With ammonium acetate In acetic acid at 100℃; for 1h; 118.B To a solution of 3-(pyridin-2-yl)benzaldehyde (813 mg, 4.4 mmol) in 8 mL AcOH was added nitromethane (1.5 mL, 27.9 mmol) followed by NH4OAc (1.51 g, 19.6 mmol). The mixture was heated to 100° C. for 1 h and then cooled to RT. After removing one-half of the solvent volume in vacuo, the concentrated solution was diluted with 100 mL EtOAc, washed with saturated NaHCO3 and dried over Na2SO4. The solution was filtered, concentrated and purified through a short plug of SiO2 with 25% EtOAc/hexane as eluant to give a yellow crystalline solid. MS m/z 227 (MH)+.
YieldReaction ConditionsOperation in experiment
R.16 4-(3-Pyridazinyl)benzaldehyde REFERENCE EXAMPLE 16 4-(3-Pyridazinyl)benzaldehyde The title compound was prepared by a procedure analogous to Reference Example 13 by substituting 3-chloropyridazine (prepared as described in WO 9724124) for the 2-chloro-4-methoxypyrimidine of Reference Example 13. MS 185 (M+H)+.
R.17 4-Pyrazinylbenzaldehyde REFERENCE EXAMPLE 17 4-Pyrazinylbenzaldehyde The title compound was prepared by a procedure analogous to Reference Example 13 by substituting chloropyrazine for the 2-chloro-4-methoxypyrimidine of Reference Example 13. MS 185 (M+H)+.
R.18 4-(4-Pyrimidinyl)benzaldehyde REFERENCE EXAMPLE 18 4-(4-Pyrimidinyl)benzaldehyde The title compound was prepared by a procedure analogous to Reference Example 13 by substituting 4-chloropyrimidine hydrochloride (prepared as described in WO 9821188) for the 2-chloro-4-methoxypyrimidine of Reference Example 13. MS 185 (M+H)+.
R.26.B Step B Step B The title compound was prepared by a procedure analogous to Reference Example 24 by substituting the product of step A for the 3-formylphenylboronic acid of Reference Example 24. MS 203 (M+H)+.
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 95℃; Inert atmosphere; 28 Example 28: Preparation of [3,4'-bipyridine]-6-carbaldehyde (Intermediate 24a) General procedure: Add 4-pyridineboronic acid (148mg, 1.2mmol), 5-bromopyridine-2-carbaldehyde(185mg, 1mmol) into a 50mL two-necked flask, bis(triphenylphosphine)palladium(II) dichloride(35mg, 0.05mmol),Potassium carbonate (276 mg, 2 mmol) and 20 mL 4:1 1,4-dioxane/water. After replacing with argon three times, the reaction was carried out at 95°C overnight. The next day, the reaction solution was cooled to room temperature, filtered using Celite, evaporated under reduced pressure to remove the solvent, purified by column chromatography, eluted with PE/EA, and evaporated under reduced pressure to remove the solvent.97 mg of colorless oily liquid was obtained, and the yield was 52.72%.

  • 16
  • [ 109-04-6 ]
  • aq. Na2CO3 [ No CAS ]
  • [ 87199-16-4 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
1.03 g (89%) In methanol; toluene R.11 3-(2-pyridinyl)benzaldehyde REFERENCE EXAMPLE 11 3-(2-pyridinyl)benzaldehyde 2M aq. Na2CO3 (5 mL) and a solution of 3-formylphenylboronic acid (1.14 g, 7.60 mmol) in methanol (5 mL) were added to a solution of 2-bromopyridine (1.00 g, 6.33 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) in toluene (10 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.03 g (89%) of the title compound. MS 184 (M+H)+.
1.03 g (89%) In methanol; toluene R.23 3-(2-Pyridinyl)benzaldehyde REFERENCE EXAMPLE 23 3-(2-Pyridinyl)benzaldehyde 2M aq. Na2CO3 (5 mL) and a solution of 3-formylphenylboronic acid (1.14 g, 7.60 mmol) in methanol (5 mL) were added to a solution of 2-bromopyridine (1.00 g, 6.33 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) in toluene (10 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.03 g (89%) of the title compound. MS 184(M+H)+.
1.03 g (89%) In methanol; toluene R.11 3-(2-pyridinyl)benzaldehyde Reference Example 11 3-(2-pyridinyl)benzaldehyde 2M aq. Na2CO3 (5 mL) and a solution of 3-formylphenylboronic acid (1.14 g, 7.60 mmol) in methanol (5 mL) were added to a solution of 2-bromopyridine (1.00 g, 6.33 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) in toluene (10 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.03 g (89%) of the title compound. MS 184 (M+H)+.
YieldReaction ConditionsOperation in experiment
R.19 4-(5-nitro-2-pyridinyl)benzaldehyde Reference Example 19 4-(5-nitro-2-pyridinyl)benzaldehyde The title compound was prepared by a procedure analogous to Reference Example 11 by substituting 4-formylphenylboronic acid and 2-bromo-5-nitropyridine for the 3-formylphenylboronic acid and 2-bromopyridine, respectively, of Reference Example 11. MS 229 (M+H)+.
  • 18
  • [ 109-04-6 ]
  • [ 497-19-8 ]
  • [ 73183-34-3 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In methanol; 5-bromo-2-(3,4-dichloro-phenoxy)-benzaldehyde; N,N-dimethyl-formamide 20 5-(2-Pyridyl)benzaldehyde Preparation 20 5-(2-Pyridyl)benzaldehyde Under N2 in a flame-dried 25 mL round bottomed flask fitted with a magnetic stirrer was placed 200 mg (0.58 mmol) of 5-bromo-2-(3,4-dichlorophenoxy)benzaldehyde, 162 mg (0.64 mmol) of bis(pinacolato)diboron (Frontier Scientific Co.), 170 mg (1.7 mmol) of potassium acetate and 13 mg (0.018 mmol) of dichloro [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (PdCl2(dppf), Strem Chemicals) in 5 mL of anhydrous DMF. The mixture was degassed with N2 for 5 min. and then heated at 80° C. for 2.5 hr. To this was added 110 μL (1.2 mmol) of 2-bromopyridine, followed by 13 mg of PdCl2(dppf) and 0.7 mL of 2 N aqueous Na2CO3. The mixture was again heated to 80° C. under N2 for a total of 10.5 hr, then allowed to cool to room temperature overnight. The mixture was partitioned between EtOAc and H2O, the organic layer was washed with water, brine and dried over Na2CO3, then concentrated in vacuo to an oil, 359 mg. Chromatography on silica gel, eluding with a gradient system of CHCl3 (100-97% and CH3OH (0-3%) gave the title product as a light brown oil, 44 mg. Mass spectrum (GCMS, m/z): 346 (m+2), 344 (m+).
  • 19
  • [ 75-52-5 ]
  • [ 85553-53-3 ]
  • C13H10N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; acetic acid at 100℃; for 2h; 84.1.2 To a mixture of 3-pyridin-2-yl-benzaldehyde (290 mg, 1.6 mmol) described in Manufacturing Example 84-1-1 and acetic acid (5 mL) were added nitromethane (0.65 mL, 12 mmol) and ammonium acetate (370 mg, 4.8 mmol), which was stirred for 2 hours at 100° C. The reaction mixture was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. A mixture of dimethyl sulfoxide (6 mL) and acetic acid (0.4 mL) was added to the resulting residue, and sodium borohydride (97 mg, 2.6 mmol) was added at room temperature while cooling appropriately. The reaction mixture was stirred for 10 minutes at the same temperature. Water was added to the reaction mixture at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The resulting residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (260 mg, 71%). 1H-NMR Spectrum (CDCl3) δ (ppm): 3.41 (2H, t, J=7.5 Hz), 4.67 (2H, t, J=7.5 Hz), 7.24-7.27 (2H, m), 7.44 (1H, t, J=7.7 Hz), 7.70-7.79 (2H, m), 7.85 (1H, d, J=7.9 Hz), 7.90 (1H, s), 8.68-8.70 (1H, m).
  • 20
  • [ 3132-99-8 ]
  • [ 17997-47-6 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 43h;
58% In toluene for 5h; Heating / reflux; 84.1.1 To a mixture of 3-bromobenzaldehyde (930 mg, 5.0 mmol) and toluene (10 mL) were added tri-n-butyl (2-pyridyl) tin (2.1 g, 5.6 mmol) and bis(triphenylphosphine)palladium(II) chloride (350 mg, 0.50 mmol), and the reaction mixture was refluxed for 5 hours. The reaction mixture was cooled to room temperature, and saturated aqueous potassium fluoride solution (1 mL) was added at that temperature and stirred for 30 minutes at room temperature. Water and ethyl acetate were added to the reaction mixture, which was then filtered through a Celite pad. The organic layer of the filtrate was separated and washed with saturated aqueous sodium chloride. The solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (530 mg, 58%). 1H-NMR Spectrum (CDCl3) δ (ppm): 7.28-7.32 (1H, m), 7.65 (1H, t, J=7.7 Hz), 7.80-7.82 (2H, m), 7.93-7.95 (1H, m), 8.29-8.31 (1H, m), 8.50-8.51 (1H, m), 8.72-8.74 (1H, m), 10.12 (1H, s).
With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 36h; Inert atmosphere;
  • 21
  • [ 35160-95-3 ]
  • [ 85553-53-3 ]
  • [ 1211986-33-2 ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: (2-naphthalenylmethyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.583333h; Inert atmosphere; Stage #2: 3-(2-pyridinyl)benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
With n-butyllithium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
  • 22
  • [ 100-58-3 ]
  • [ 85553-53-3 ]
  • [ 1334336-34-3 ]
YieldReaction ConditionsOperation in experiment
43% In tetrahydrofuran; diethyl ether at -10 - 0℃; for 1.16667h;
  • 23
  • [ 142-08-5 ]
  • [ 87199-16-4 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 2-hydroxypyridin With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 3-Formylphenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Inert atmosphere;
  • 24
  • [ 85553-53-3 ]
  • [ 1211986-36-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: iodine / toluene / 18 h / Inert atmosphere; Irradiation
  • 25
  • [ 85553-53-3 ]
  • C26H37N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 4 h / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2.2: 2.5 h / 0 - 20 °C
  • 26
  • [ 85553-53-3 ]
  • C35H40ClN3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 4 h / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2.2: 2.5 h / 0 - 20 °C 3.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 27
  • [ 85553-53-3 ]
  • [ 1396789-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 4 h / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2.2: 2.5 h / 0 - 20 °C 3.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
  • 28
  • [ 85553-53-3 ]
  • [ 177906-48-8 ]
  • C23H31N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-(2-pyridinyl)benzaldehyde; trans-N-Boc-1,4-cyclohexanediamine In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 0 - 20℃; for 4h;
  • 30
  • [ 85553-53-3 ]
  • C36H20IrN7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2-ethoxy-ethanol; water / 24 h / Inert atmosphere; Reflux 2: 1,2-dichloro-ethane / 20 h / Inert atmosphere; Reflux 3: pyridine / ethanol / 12 h / Reflux
  • 31
  • [ 85553-53-3 ]
  • C30H20IrN3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-ethoxy-ethanol; water / 24 h / Inert atmosphere; Reflux 2: 1,2-dichloro-ethane / 20 h / Inert atmosphere; Reflux
  • 32
  • iridium(III) chloride trihydrate [ No CAS ]
  • [ 85553-53-3 ]
  • [(3-(2-pyridyl)benzaldehyde)2Ir(μ-Cl)]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 2-ethoxy-ethanol; water for 24h; Inert atmosphere; Reflux; 3.3.1 Typical procedure for synthesizing complexes 2a, 2b and 2c General procedure: A mixture of the ligands 1a (1.375 g, 7.5 mmol), 1b (1.375 g, 7.5 mmol) or 1c (1.478 g, 7.5 mmol), IrCl3*3H2O (1.1 g, 3.5 mmol), 2-ethoxyethanol (150 mL)/distilled H2O (50 mL) was refluxed under argon for 24 h. After cooling to room temperature, distilled H2O (150 mL) was added and the resulting precipitate was collected by filteration and washed with water, ethanol and hexane successively. After drying, the crude product was directly used for next step without further purifying. A solution of the dimer (0.5 mmol) and picolinic acid (0.15 g, 1.25 mmol) in 1,2-dichloroethane (50 mL) was refluxed under argon for 20 h, then 1,2-dichloroethane was evaporated and the resulting precipitate was directly dissolved in CH2Cl2 and subjected to flash chromatography on silica gel using CH2Cl2 and methanol as eluent to afford the desired Iridium complexes.
In 2-ethoxy-ethanol; water for 24h; Reflux; Inert atmosphere;
  • 33
  • [ 85553-53-3 ]
  • (±)-cis-1-(4-methoxyphenyl)-3-phenoxy-4-(4-(pyridin-2-yl)phenyl)azetidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium sulfate / dichloromethane / 15 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.2: 16 h / 20 °C / Inert atmosphere
  • 34
  • [ 85553-53-3 ]
  • (±)-cis-1-(4-methoxyphenyl)-3-phenoxy-4-(3-(pyridin-2-yl)phenyl)azetidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium sulfate / dichloromethane / 15 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.2: 16 h / 20 °C / Inert atmosphere
  • 35
  • [ 85553-53-3 ]
  • [ 1515862-09-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium sulfate / dichloromethane / 15 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.2: 16 h / 20 °C / Inert atmosphere
  • 36
  • [ 104-94-9 ]
  • [ 85553-53-3 ]
  • 4-methoxy-N-(3-(pyridin-2-yl)benzylidene)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium sulfate In dichloromethane at 20℃; for 15h;
  • 37
  • [ 85553-53-3 ]
  • C22H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 12 h 2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 24 h / 20 °C
  • 38
  • [ 85553-53-3 ]
  • tert-butyl (4-(hydroxymethyl)-2-(pyridin-2-yl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 12 h 2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer / water / 16 h / 60 °C / Schlenk technique
  • 39
  • [ 85553-53-3 ]
  • 4-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)benzyl-2-((tert-butoxycarbonyl)amino)-3-methylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 12 h 2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 24 h / 20 °C 3: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer / water / 16 h / 60 °C / Schlenk technique
  • 40
  • [ 17508-16-6 ]
  • [ 85553-53-3 ]
  • tert-butyl (4-formyl-2-(pyridin-2-yl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 60℃; for 16h; Schlenk technique;
  • 41
  • [ 667-27-6 ]
  • [ 85553-53-3 ]
  • C16H15F2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With zinc In tetrahydrofuran at 75℃; for 2h; Inert atmosphere; 20 Example 20 [000367] To a solution of Compound 20A (2.2 g, 12 mmol) in anhydrous tetrahydrofuran (80 mL) was added zinc (1.01 g, 15.6 mmol). The mixture was heated at 75 °C under N2 atmosphere and ethyl 2-bromo-2, 2-difluoroacetate (1.9 mL, 15 mmol) was slowly added. The mixture was heated under the same conditions for 2 h. After cooling, it was filtered. The filtrate was concentrated to give a crude product, which was purified by silica gel column chromatography (ethyl acetate in petroleum ether, 20% v/v) to afford Compound 20B (1.9 g, yield 58%) as a colorless oil. LCMS (m/z): 309 [M+l]+.
  • 42
  • [ 85553-53-3 ]
  • C20H17F2N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc / tetrahydrofuran / 2 h / 75 °C / Inert atmosphere 2: dichloromethane / 3 h / 72 °C
  • 43
  • [ 85553-53-3 ]
  • C16H15F2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: zinc / tetrahydrofuran / 2 h / 75 °C / Inert atmosphere 2: dichloromethane / 3 h / 72 °C 3: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3 h / 110 °C
  • 44
  • [ 85553-53-3 ]
  • C14H11F2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: zinc / tetrahydrofuran / 2 h / 75 °C / Inert atmosphere 2: dichloromethane / 3 h / 72 °C 3: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3 h / 110 °C 4: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 25 °C
  • 45
  • [ 85553-53-3 ]
  • N-((1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2,2-difluoro-3-(3-(pyridin-2-yl)phenyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: zinc / tetrahydrofuran / 2 h / 75 °C / Inert atmosphere 2: dichloromethane / 3 h / 72 °C 3: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3 h / 110 °C 4: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 25 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 25 °C
  • 46
  • [ 105-56-6 ]
  • [ 85553-53-3 ]
  • [ 105-53-3 ]
  • C21H18N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With sodium acetate; sodium bromide In methanol at 0℃; for 0.5h; Electrolysis; stereoselective reaction;
  • 47
  • C164H148Cl2Ir2N8O4 [ No CAS ]
  • [ 85553-53-3 ]
  • bis[9-(4-(2-ethylhexyloxy)phenyl)-3-(4-phenylquinolin-2-yl)-9H-carbazole] [3-(pyridin-2-yl) benzaldehyde]iridium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With silver trifluoromethanesulfonate In diethylene glycol dimethyl ether at 110℃; for 13h; Inert atmosphere;
28% With silver trifluoromethanesulfonate In diethylene glycol dimethyl ether at 110℃; Inert atmosphere; Darkness; 2.3 reaction condition 3: the dimer 5 (552mg, 0.2mmol), 3- (pyridin-2-yl) benzaldehyde (402mg, 2.2mmol) and silver trifluoromethanesulfonate (128mg, 0.5mmol) placed in the dark 10mL within the reaction tube, the replacement of nitrogen by adding 5 ml diethylene glycol dimethyl ether, in 110 °C reaction under 13h, cooled to the room temperature end of the reaction, the obtained extraction and chromatographic column purification Ir- cHO 170 mg), yield 28%.
  • 48
  • N,N′-bis(2′,6′-diisopropylphenyl)-1-amino-perylene-3,4:9,10-tetracarboxylic acid bisimide [ No CAS ]
  • [ 85553-53-3 ]
  • N,N′-bis(2′,6′-diisopropylphenyl)-13-(3″-(pyridin-2‴-yl)-phenyl)-azabenzo[pqr]-perylene-3,4:9,10-tetracarboxylic acid bisimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% Stage #1: N,N′-bis(2′,6′-diisopropylphenyl)-1-amino-perylene-3,4:9,10-tetracarboxylic acid bisimide; 3-(2-pyridinyl)benzaldehyde With trifluoroacetic acid In N,N-dimethyl-formamide at 110℃; for 0.5h; Molecular sieve; Schlenk technique; Inert atmosphere; Stage #2: With oxygen In N,N-dimethyl-formamide at 110℃; Molecular sieve; Schlenk technique;
  • 49
  • [ 95-54-5 ]
  • [ 85553-53-3 ]
  • C18H13N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In water; N,N-dimethyl-formamide at 80℃;
  • 50
  • [ 131-62-4 ]
  • [ 85553-53-3 ]
  • C19H12INO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 55℃; for 12h; General procedure: [Cp*RhCl2]2 (2.5 mol %), Cu(OTf)2 (5 mol %), 1a (0.2 mmol), 2a (0.24 mmol, 1.2 equiv) and DCE (2 mL) were added to a test tube. The reaction mixture was stirred at 55 oC for 12 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using PE/EA (5:1) to afford the title compound 3a.
  • 51
  • [ 941-55-9 ]
  • [ 85553-53-3 ]
  • N-(4-formyl-2-(pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bromopentacarbonylmanganese(I); tetrabutylammomium bromide In water at 120℃; for 16h; regioselective reaction;
  • 52
  • [ 67-68-5 ]
  • [ 85553-53-3 ]
  • 4-(methylthio)-3-(pyridin-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With copper(II) sulfate; glycine at 140℃; for 24h; Inert atmosphere; regioselective reaction; General procedure for C-H methylthiolation of 2-phenyl pyridines General procedure: In an argon-filled screwed text tube, 2-phenylpyridines (0.5 mmol), anhydrous copper sulfate (79.9 mg, 0.5 mmol), glycine (3.8 mg, 0.05 mmol), and dimethyl sulfoxide (0.1 mL, 1.4 mmol) were added. The reaction mixture was stirred at 140 °C in a preheated oil bath for 24 h. The temperature was lowered to room temperature, and water (10 mL) was added. The reaction mixture was extracted with ethyl acetate (10 mL x 3), and the organic layer was collected, washed with brine, dried with anhydrous Na2SO4 and concentrated by a rotary evaporator. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluent.
  • 53
  • [ 108-88-3 ]
  • [ 85553-53-3 ]
  • 2-phenyl-1-(3-(pyridin-2-yl)phenyl)ethan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With sodium hexamethyldisilazane; caesium carbonate at 110℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;
  • 54
  • [ 17084-13-8 ]
  • iridium(III) chloride trihydrate [ No CAS ]
  • [ 91804-75-0 ]
  • [ 85553-53-3 ]
  • C36H23ClIrN4O2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Under nitrogen protection, 1.0 mmol of IrCl3 · 3H2O was added to 40 mL of a 60% 2-ethoxyethanol aqueous solution and mixed, and magnetically stirred for 25 minutes.Add 2.0 mmol of 3- (2-pyridyl) -benzaldehyde, heat at 110 C and condense and reflux. Stir the reaction for 25 hours, then cool to room temperature and perform suction filtration under reduced pressure. Ionized water, ethanol and n-hexane were washed sequentially, and the chlorine bridge dimer was obtained after vacuum drying;2) Synthesis of iridium complex with 3- (2-pyridyl) -benzaldehyde as the main ligandUnder the protection of nitrogen, take 0.1mmol of the chlorine bridge dimer prepared in step 1) and 0.2mmol of <strong>[91804-75-0]5-aldehyde-1,10 phenanthroline</strong>, add it to 40mL of dichloromethane solvent, heat and condense at 40 C and reflux. It was stirred for 14 hours, and then cooled to room temperature to form a cooling liquid. Potassium hexafluorophosphate was added so that the molar ratio of potassium hexafluorophosphate to IrCl3 · 3H2O was 10: 1, stirred at room temperature for 2 hours, and then the solvent was removed by rotary evaporation. Then, 1 mL of dichloromethane and 40 mL of ethanol were used as developing agents for chromatography in a silica gel column. After purification, an iridium complex with 3- (2-pyridyl) -benzaldehyde as the main ligand was obtained.
  • 55
  • [ 1008-89-5 ]
  • [ 75-25-2 ]
  • [ 85553-53-3 ]
YieldReaction ConditionsOperation in experiment
53% With N-acetylleucine; bis(4-methylisopropylphenyl)ruthenium(II) diacetate; potassium carbonate In acetonitrile at 120℃; for 24h; Sealed tube; Inert atmosphere; 1 Example 1: In a 20 mL pressure-resistant reaction tube, add 31 mg (0.2 mmol) of 2-phenylpyridine, 151 mg (0.6 mmol) of carbon tribromide, and 6 mg (0.01 mmol) of bis (4-methylisopropylphenyl) ruthenium diacetate. 11mg (0.06mmol) acetyl leucine, 82mg (0.6mmol) potassium carbonate,1mL acetonitrile, sealed under nitrogen, heated to 120°C reaction, stirred for 24 hours,After the reaction, column chromatography separated the target product 3- (2-pyridyl) benzaldehyde 19mg,The yield is 53%.
53% With N-Ac-Leu; [Ru(OAc)2(p-cymene)]; potassium carbonate In acetonitrile at 120℃; for 24h; Sealed tube; Inert atmosphere;
53% With [RhCl2(p-cymene)]2; N-acetylleucine; potassium carbonate In acetonitrile at 120℃; for 24h; Sealed tube; Inert atmosphere; 1 Raw material preparation example 1 shown in formula I: In a 20 mL pressure-resistant reaction tube, add 31 mg (0.2 mmol) of 2-phenylpyridine, 151 mg (0.6 mmol) of carbon tribromide, and 6 mg (0.01 mmol) of dichlorobis(4-methylisopropylphenyl)ruthenium. 11mg (0.06mmol) acetylleucine, 82mg (0.6mmol) potassium carbonate, 1mL acetonitrile, sealed under nitrogen, heated to 120 °C reaction, stirred for 24 hours, after the reaction, column chromatography to obtain the target product 3-(2-pyridyl)benzaldehyde 19mg, yield 53%.
53% With N-acetylleucine; potassium carbonate In acetonitrile at 120℃; for 24h; Inert atmosphere; Sealed tube; 1 Preparation Example 1 of the raw material shown in Formula I In a 20 mL pressure-resistant reaction tube, add 31 mg (0.2 mmol) of 2-phenylpyridine, 151 mg (0.6 mmol) of tribromomethane,6 mg (0.01 mmol) bis(4-methylisopropylphenyl)ruthenium diacetate, 11 mg (0.06 mmol) acetylleucine, 82 mg (0.6 mmol) potassium carbonate, 1 mL acetonitrile, sealed under nitrogen. The reaction was heated to 120 ° C and stirred for 24 hours. After the reaction, the column was separated by chromatography.19 mg of the target product 3-(2-pyridyl)benzaldehyde was obtained with a yield of 53%.

  • 56
  • [ 85553-53-3 ]
  • [ 1092657-35-6 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 3-(2-pyridinyl)benzaldehyde With sodium tetrahydroborate In methanol at 20℃; for 12h; Stage #2: With hydrogenchloride In water Reflux;
  • 57
  • [ 85553-53-3 ]
  • [ 4350-51-0 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 3-(2-pyridinyl)benzaldehyde With tert.-butylhydroperoxide; ammonium acetate; iodine Stage #2: With sodium carbonate In ethanol at 50℃; for 8h;
88% With tert.-butylhydroperoxide; ammonium acetate; iodine; sodium carbonate In ethanol at 50℃; for 8h; 1 Preparation Example 1 of meta-cyano aromatic compound Add 92 mg (0.5 mmol) of 3-(2-pyridyl)benzaldehyde, 65 mg (0.75 mmol) of ammonium acetate to a 20 mL pressure-resistant reaction tube,1.6 mg (0.0125 mmol) of iodine, 50 mg (0.55 mmol) of tert-butyl hydroperoxide, 53 mg (0.5 mmol) of sodium carbonate,1mL ethanol, heated to 50 ° C, and stirred for 8 hours. After the reaction, the column chromatography was used to separate it.165 mg of the target product 3-(2-pyridyl)benzonitrile was obtained with a yield of 88%.
  • 58
  • [ 85553-53-3 ]
  • [ 74-88-4 ]
  • [ 98061-20-2 ]
  • 59
  • [ 1080-32-6 ]
  • [ 85553-53-3 ]
  • (E)-2-(3-styrylphenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With sodium methylate In N,N-dimethyl-formamide at 20℃;
  • 60
  • [ 1080-32-6 ]
  • [ 85553-53-3 ]
  • 2-(3-styrenylphenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With sodium methylate In N,N-dimethyl-formamide at 20℃; for 2h; 1 Preparation Example 2: Meta-alkenyl aromatic compound: Add 92 mg (0.5 mmol) 3-(2-pyridyl)benzaldehyde, 114 mg (0.5 mmol) benzyl diethyl phosphate, and 27 mg (0.5 mmol) sodium methoxide to a 20 mL pressure-resistant reaction tube.1mL DMF, stirred at room temperature for 2 hours, after the reaction, column chromatography to obtain the target product 2-(3-styrene phenyl)pyridine 121mg, yield 94%.
  • 61
  • [ 14078-85-4 ]
  • [ 85553-53-3 ]
  • C15H21B10NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; copper diacetate; silver trifluoromethanesulfonate; lithium carbonate In toluene at 130℃; for 12h; Sealed tube; Inert atmosphere;
  • 62
  • [ 141-43-5 ]
  • [ 85553-53-3 ]
  • [ 1440513-11-0 ]
YieldReaction ConditionsOperation in experiment
22% Stage #1: ethanolamine; 3-(2-pyridinyl)benzaldehyde In dichloromethane at 20℃; for 19h; Molecular sieve; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; Molecular sieve;
  • 63
  • [ 2749-11-3 ]
  • [ 85553-53-3 ]
  • C15H14N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: (S)-Alaninol; 3-(2-pyridinyl)benzaldehyde In dichloromethane at 20℃; for 19h; Molecular sieve; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; Molecular sieve;
  • 64
  • [ 2026-48-4 ]
  • [ 85553-53-3 ]
  • C17H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% Stage #1: (S)-valinol; 3-(2-pyridinyl)benzaldehyde In dichloromethane at 20℃; for 19h; Molecular sieve; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; Molecular sieve;
  • 65
  • [ 4276-09-9 ]
  • [ 85553-53-3 ]
  • C17H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: (R)-2-amino-3-methylbutanol; 3-(2-pyridinyl)benzaldehyde In dichloromethane at 20℃; for 19h; Molecular sieve; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; Molecular sieve;
  • 66
  • (1S,2R)-1-amino-2-indanol [ No CAS ]
  • [ 85553-53-3 ]
  • C21H16N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: (1S,2R)-1-amino-2-indanol; 3-(2-pyridinyl)benzaldehyde In dichloromethane at 20℃; for 19h; Molecular sieve; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; Molecular sieve;
  • 67
  • [ 533-31-3 ]
  • [ 122536-76-9 ]
  • [ 85553-53-3 ]
  • tert-butyl ((3R)-1-((6-hydroxybenzo[d][1,3]dioxol-5-yl)(3-(pyridin-2-yl)phenyl)methyl)pyrrolidine-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.6% In ethanol; hexane at 20℃; 4.1.1. 6-(Pyridin-4-yl(pyrrolidine-1-yl)methyl)benzo[d][1,3]dioxol-5-ol (9) General procedure: A solution of Sesamol (17a, 138 mg, 1 mmol), 4-pyridinecarboxaldehyde (18a, 107 mg, 1 mmol) and pyrrolidine(16a, 71 mg, 1 mmol) in 1 mL 1:1 ethanol/n-hexane was stirred atroom temperature overnight. After the reaction was completedmonitored by TLC, the solution was concentrated. The residue waspurified by Isolera Biotage LPLC (PE/EA 1:1) to give 9 (247 mg,82.9%) as a foam solid.
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