Home Cart 0 Sign in  
X

[ CAS No. 103441-60-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 103441-60-7
Chemical Structure| 103441-60-7
Chemical Structure| 103441-60-7
Structure of 103441-60-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 103441-60-7 ]

Related Doc. of [ 103441-60-7 ]

Alternatived Products of [ 103441-60-7 ]

Product Details of [ 103441-60-7 ]

CAS No. :103441-60-7 MDL No. :MFCD12923249
Formula : C9H9IO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HQVMBKJRAJYZQK-UHFFFAOYSA-N
M.W :276.07 Pubchem ID :13924925
Synonyms :

Calculated chemistry of [ 103441-60-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.4
TPSA : 26.3 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 3.11
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.74
Solubility : 0.0499 mg/ml ; 0.000181 mol/l
Class : Soluble
Log S (Ali) : -3.32
Solubility : 0.132 mg/ml ; 0.000478 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0428 mg/ml ; 0.000155 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.99

Safety of [ 103441-60-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 103441-60-7 ]

* 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 [ 103441-60-7 ]

[ 103441-60-7 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 609-73-4 ]
  • [ 103441-60-7 ]
  • [ 855255-31-1 ]
YieldReaction ConditionsOperation in experiment
With copper at 250℃; Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge;
  • 2
  • [ 103441-60-7 ]
  • [ 19634-85-6 ]
YieldReaction ConditionsOperation in experiment
With copper at 220℃; man verseift das Reaktionsprodukt mit verd. Natronlauge;
With copper at 270℃; Erwaermen des Reaktionsprodukts mit wss. Natronlauge;
Multi-step reaction with 2 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating
Multi-step reaction with 2 steps 1: 92 percent / dendritic copper / dimethylformamide / 150 °C 2: H2O, KOH / ethanol / 60 °C
Multi-step reaction with 2 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux

  • 3
  • [ 103441-60-7 ]
  • [ 83527-41-7 ]
YieldReaction ConditionsOperation in experiment
93% With copper In N,N-dimethyl-formamide for 5.5h; Heating;
92% With dendritic copper In N,N-dimethyl-formamide at 150℃;
88% With activated copper bronze powder In N,N-dimethyl-formamide for 5h; Inert atmosphere; Reflux; 4.2.5. Step 5: synthesis of bitoluyl diester (8)5a,3j To a solution of compound 7 (1g, 3.7mmol) in N,N-dimethyl formamide (3.3mL) was added activated copper bronze powder (0.55g) with stirring. The reaction was then slowly refluxed under inert atmosphere. It was stopped after 5h and cooled to rt and the copper was filtered off and washed with methylene chloride (3×5mL). Then organic layer was washed with HCl (1M, 2mL), aqueous potassium hydrogen carbonate (3mL) and brine (3mL) and then dried over MgSO4. The solvent was evaporated to afford a crude residue. Purification using column chromatography (5-20% EtOAc/hexane), produced dimethyl 6,6-dimethylbiphenyl-2,2 dicarboxylate 8 (0.97g, 88%) as a light yellow oil. δH (300MHz, CDCl3) 1.92 (6H, s, Me), 3.57 (6H, s, CO2Me), 7.31-7.37 (2H, t, J 7.6Hz, Ph), 7.45 (2H, d, J 7.5Hz, Ph), 7.87 (2H, d, J 7.7Hz, Ph).
85% With tetra-(n-butyl)ammonium iodide; sodium hydride; zinc In toluene at 90℃; for 1.5h;
80% With copper In N,N-dimethyl-formamide for 5h; Heating;
65% With bis(triphenylphosphine)nickel(II) chloride; sodium hydride; triphenylphosphine In toluene at 70 - 90℃;
With copper (+-)-6,6'-dimethyl-diphenic acid dimethyl ester;
1.68 g In N,N-dimethyl-formamide for 4h; Heating;

  • 4
  • [ 67-56-1 ]
  • [ 108078-14-4 ]
  • [ 103441-60-7 ]
YieldReaction ConditionsOperation in experiment
630 mg With diazomethyl-trimethyl-silane; In diethyl ether; dichloromethane; at 0 - 20℃; for 1.5h; <strong>[108078-14-4]2-iodo-3-methylbenzoic acid</strong> (595mg, 2.27mmol) was dissolved in DCM/MeOH=1/1 (5m1) at 000, then TMS-CH2N2 (2M in Et20, 1 .4m1, 2.8mmol) was added. After 1,5 hours at RT solvents were evaporated. Yield 630mg yellow oil.1HNMR (CDCI3) 5 ppm = = 7.42 - 7.32 (m, 2 H), 7.32 - 7.25 (m, 1 H, under the solvent peak), 2.55 (s, 3 H).
630 mg With trimethylsilyl diazomethane; In diethyl ether; dichloromethane; at 0 - 20℃; for 1.5h; <strong>[108078-14-4]2-iodo-3-methylbenzoic acid</strong> (595 mg, 2.27 mmol) was dissolved in DCM/MeOH=1/1 (5 ml) at 0 C., then TMS-CH2N2 (2M in Et2O, 1.4 ml, 2.8 mmol) was added. After 1.5 hours at RT solvents were evaporated. Yield 630 mg yellow oil. 1HNMR (CDCl3) delta ppm==7.42-7.32 (m, 2H), 7.32-7.25 (m, 1H, under the solvent peak), 2.55 (s, 3H).
  • 5
  • [ 5089-33-8 ]
  • [ 103441-60-7 ]
  • 4'-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-6-methyl-biphenyl-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine)nickel(0); tert.-butyl lithium; zinc(II) chloride Multistep reaction;
  • 6
  • [ 108078-14-4 ]
  • [ 74-88-4 ]
  • [ 103441-60-7 ]
  • 7
  • (+/-)-8-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2-carbaldehyde [ No CAS ]
  • [ 103441-60-7 ]
  • (+/-)-methyl 2-(8-formyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); CyJohnPhos In N,N-dimethyl-formamide at 105℃; for 20h;
  • 9
  • [ 5437-38-7 ]
  • [ 103441-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr 2.1: H2SO4 / H2O / 1 h / 20 °C 2.2: NaNO2 / H2O / 1.5 h / 10 °C 2.3: 84 percent / KI; Cu powder / H2O / 30 °C 3.1: 90 percent / SOCl2 / 3 h / Heating
Multi-step reaction with 3 steps 1: 89 percent / tin, hydrochloric acid / ethanol / 1.5 h / 70 °C 2: 1.) conc. H2SO4, NaNO2; 2.) KI, copper / 1.) water, r.t., 1 h; 2.) water, 30 deg C, 3 h 3: 94 percent / hydrogen chloride / 1 h / Heating
Multi-step reaction with 3 steps 1.1: thionyl chloride / 10 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / ethanol / 10 h / 20 °C 3.1: hydrogenchloride / water / 0.25 h / 0 °C / Inert atmosphere 3.2: 0 °C / Inert atmosphere 3.3: 0 - 20 °C
  • 10
  • [ 4389-45-1 ]
  • [ 103441-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: H2SO4 / H2O / 1 h / 20 °C 1.2: NaNO2 / H2O / 1.5 h / 10 °C 1.3: 84 percent / KI; Cu powder / H2O / 30 °C 2.1: 90 percent / SOCl2 / 3 h / Heating
Multi-step reaction with 2 steps 1: 1.) conc. H2SO4, NaNO2; 2.) KI, copper / 1.) water, r.t., 1 h; 2.) water, 30 deg C, 3 h 2: 94 percent / hydrogen chloride / 1 h / Heating
Multi-step reaction with 2 steps 1.1: NaNO2; sulfuric acid / lithium hydroxide monohydrate / 0.5 h / 5 °C / Inert atmosphere; Schlenk technique 1.2: 100 °C / Inert atmosphere; Schlenk technique 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere; Schlenk technique 2.2: 16 h / 20 °C / Inert atmosphere; Schlenk technique
  • 11
  • [ 99-04-7 ]
  • [ 103441-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 46 percent / HNO3 / 1 h / -10 °C 2.1: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr 3.1: H2SO4 / H2O / 1 h / 20 °C 3.2: NaNO2 / H2O / 1.5 h / 10 °C 3.3: 84 percent / KI; Cu powder / H2O / 30 °C 4.1: 90 percent / SOCl2 / 3 h / Heating
Multi-step reaction with 4 steps 1.1: nitric acid / 1 h / -10 °C / Inert atmosphere 2.1: thionyl chloride / 10 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogen; palladium 10% on activated carbon / ethanol / 10 h / 20 °C 4.1: hydrogenchloride / water / 0.25 h / 0 °C / Inert atmosphere 4.2: 0 °C / Inert atmosphere 4.3: 0 - 20 °C
  • 12
  • [ 103441-60-7 ]
  • [ 302342-86-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C
Multi-step reaction with 3 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere
  • 13
  • [ 103441-60-7 ]
  • (S,S,S)-2,2'-bi-o-tolyl-1,1-di t-butyl bisoxazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C 5: thionyl chloride / CH2Cl2 / 24 h / 20 °C 6: K2CO3 / acetonitrile; H2O / 8 h / Heating
  • 14
  • [ 103441-60-7 ]
  • (S,S,S)-2,2'-bi-o-tolyl-1,1-diphenyl bisoxazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: 0.65 g / CH2Cl2 / -40 - 20 °C 5: thionyl chloride / CH2Cl2 / 24 h / 20 °C 6: K2CO3 / acetonitrile; H2O / 8 h / Heating
Multi-step reaction with 5 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 4: triethylamine / dichloromethane / -40 - 20 °C / Inert atmosphere 5: dmap; p-toluenesulfonyl chloride; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere
  • 15
  • [ 103441-60-7 ]
  • (S,S,S)-6,6'-dimethyl-biphenyl-2,2'-dicarboxylic acid bis[(2-hydroxy-1-phenyl-ethyl)-amide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: 0.65 g / CH2Cl2 / -40 - 20 °C
Multi-step reaction with 4 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 4: triethylamine / dichloromethane / -40 - 20 °C / Inert atmosphere
  • 16
  • [ 103441-60-7 ]
  • (S,S,S)-2,2'-bi-o-tolyl-1,1-di i-propyl bisoxazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C 5: thionyl chloride / CH2Cl2 / 24 h / 20 °C 6: K2CO3 / acetonitrile; H2O / 8 h / Heating
Multi-step reaction with 5 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 4: triethylamine / dichloromethane / -40 - 20 °C / Inert atmosphere 5: dmap; p-toluenesulfonyl chloride; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere
  • 17
  • [ 103441-60-7 ]
  • 6,6'-Dimethyl-biphenyl-2,2'-dicarboxylic acid bis-[((S)-1-chloromethyl-2-methyl-propyl)-amide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C 5: thionyl chloride / CH2Cl2 / 24 h / 20 °C
  • 18
  • [ 103441-60-7 ]
  • (S,S,S)-6,6'-dimethyl-biphenyl-2,2'-dicarboxylic acid bis[(2-hydroxy-1-i-propyl-ethyl)-amide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C
Multi-step reaction with 4 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 4: triethylamine / dichloromethane / -40 - 20 °C / Inert atmosphere
  • 19
  • [ 103441-60-7 ]
  • 6,6'-Dimethyl-biphenyl-2,2'-dicarboxylic acid bis-[((S)-1-chloromethyl-2,2-dimethyl-propyl)-amide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C 5: thionyl chloride / CH2Cl2 / 24 h / 20 °C
  • 20
  • [ 103441-60-7 ]
  • (S,S,S)-6,6'-dimethyl-biphenyl-2,2'-dicarboxylic acid bis[(2-hydroxy-1-t-butyl-ethyl)-amide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C
  • 21
  • [ 103441-60-7 ]
  • (S,S,S)-2,2'-bi-o-tolyl-1,1-dibenzyl bisoxazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C 5: thionyl chloride / CH2Cl2 / 24 h / 20 °C 6: K2CO3 / acetonitrile; H2O / 8 h / Heating
Multi-step reaction with 5 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 4: triethylamine / dichloromethane / -40 - 20 °C / Inert atmosphere 5: dmap; p-toluenesulfonyl chloride; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere
  • 22
  • [ 103441-60-7 ]
  • (S,S,S)-6,6'-dimethyl-biphenyl-2,2'-dicarboxylic acid bis[(2-hydroxy-1-benzyl-ethyl)-amide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.68 g / Cu / dimethylformamide / 4 h / Heating 2: 1.50 g / NaOH / H2O / 6 h / Heating 3: 99 percent / oxalyl chloride; DMF / CH2Cl2 / 8 h / 20 °C 4: CH2Cl2 / -40 - 20 °C
Multi-step reaction with 4 steps 1: activated copper bronze powder / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / 4.5 h / Inert atmosphere; Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 4: triethylamine / dichloromethane / -40 - 20 °C / Inert atmosphere
  • 23
  • [ 103441-60-7 ]
  • [ 138153-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) t-BuLi, 2.) ZnCl2, 3.) Ni(PPh3)4 2: aq. HCl / 1 h 3: TFA / 24 h / Ambient temperature 4: 92 percent / LiOH / methanol; H2O; CH2Cl2 / 24 h / 50 °C
Multi-step reaction with 3 steps 2: trifluoroacetic acid (TFAA) / 24 h / Ambient temperature 3: 92 percent / lithium hydroxide, H2O / methanol; CH2Cl2 / 24 h / 50 °C
  • 24
  • [ 103441-60-7 ]
  • [ 138153-83-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: trifluoroacetic acid (TFAA) / 24 h / Ambient temperature 3: 14 percent / ammonia, trimethylaluminum / benzene; CH2Cl2 / 192 h / 40 °C
  • 25
  • [ 22223-49-0 ]
  • [ 103441-60-7 ]
YieldReaction ConditionsOperation in experiment
85% A suspension of compound 6 (1g, 6mmol) in a mixture of HCl (2.2mL, %37) and ice was stirred for 15min at 0C. Then a solution of NaNO2 (0.4g, 6mmol) in cold water (3mL) was added slowly at 0C to the reaction mixture. Then the mixture was stirred until it became homogeneous. Another round-bottom flask was charged with potassium iodide (3.46g, 20mmol) and water (8mL). The freshly prepared solution containing the diazonium salt was added to this mixture by funnel at 0C. The solution was allowed to warm slowly to rt and stirred for further 20h. The product was extracted with diethyl ether (3×8mL), the organic layer was washed with sodium thiosulfate (5mL) and the solvent was evaporated to afford compound 7 (1.41g, 85%); deltaH (300MHz, CDCl3) 2.52 (3H, s, Me), 3.92 (3H, s, CO2Me), 7.25-7.38 (3H, m, Ph); deltaC (75MHz, CDCl3) 29.7, 52.6, 100.0, 127.1, 127.8, 131.8, 138.4, 143.4, 168.8
  • 26
  • [ 103441-60-7 ]
  • [ 98-80-6 ]
  • methyl 6-methyl-[1,1'-biphenyl]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 60℃; Schlenk technique;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; palladium diacetate In 1,2-dimethoxyethane at 80℃; Inert atmosphere; Schlenk technique; 2. Preparation of starting materials[1][2] General procedure: To a 50 mL oven-dried Schlenk flask equipped with a magnetic stir bar, were added methyl 2-iodobenzoate (2.62 g, 10 mmol), arylboronic acid (15 mmol),Pd(OAc)2 (22 mg, 1 mol%), PPh3 (52 mg, 2 mol%) and K3PO4 (4.24 g, 20 mmol).The Schlenk flask was evacuated and backfilled with N2 for 3 times. Then toluene (20mL) was added. The reaction mixture was heated at 80 C. The reaction progress wasmonitored by thin-layer chromatography (TLC) analysis. After the reaction was completed, the mixture was cooled to room temperature. Then the reaction mixture was concentrated on a rotary evaporator, and purified by column chromatography(PE/EtOAc = 50/1) to give the desired ester.KOH (3.0 g, 75 mmol), MeOH (20 mL) and the desired ester were added to a50-mL of flask, and the mixture was heated at 80 oC for 2-12 h (TLC monitored). The reaction mixture was cooled to room temperature. Then the reaction mixture was acidified and extracted with DCM (3 x 30 mL). Combined organic extract was dried with Na2SO4, concentrated on a rotary evaporator and the residue was purified bycolumn chromatography on silica gel using PE/EtOAc = 5/1 as eluent to afford theproduct. To a 50 mL oven-dried Schlenk flask equipped with a magnetic stir bar, were added methyl 2-iodobenzoate (10 mmol), phenylboronic acid (15 mmol), Pd(OAc)2(112 mg, 5 mol%), DPPF (338 mg, 6 mol%) and K3PO4 (20 mmol). The Schlenk flask was evacuated and backfilled with N2 for 3 times. Then 1,2-dimethoxyethane (30 mL)was added. The reaction mixture was heated at 80 C. The reaction progress was monitored by thin-layer chromatography (TLC) analysis. After the reaction was completed, the mixture was cooled to room temperature. Then the reaction mixture was concentrated on a rotary evaporator, and purified by column chromatography(PE/EtOAc = 50/1) to give the desired ester.KOH (3.0 g, 75 mmol), MeOH (20 mL) and the desired ester were added to a 50-mL of flask, and the mixture was heated at 80 oC for 2-12 h (TLC monitored). The reaction mixture was cooled to room temperature. Then the reaction mixture was acidified and extracted with DCM (3 x 30 mL). Combined organic extract was dried with Na2SO4, concentrated on a rotary evaporator and the residue was purified by column chromatography on silica gel using PE/EtOAc = 5/1 as eluent to afford theproduct.Other reagents and solvents were purchased from commercial supplier and used without any further treatment.
  • 27
  • [ 65094-22-6 ]
  • [ 103441-60-7 ]
  • [ 1369842-38-5 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: diethyl (bromodifluoromethyl)phosphonate With zinc In 1,4-dioxane at 60℃; for 3h; Inert atmosphere; Stage #2: With copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #3: methyl 2-iodo-3-methylbenzoate In 1,4-dioxane at 60℃; for 24h; Inert atmosphere;
  • 28
  • [ 6213-94-1 ]
  • [ 103441-60-7 ]
  • methyl 2-acetyl-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 100℃; for 2h; Microwave irradiation; regioselective reaction;
  • 29
  • [ 103441-60-7 ]
  • dimethyl 6,6'-dimethyl-[1,1'-biphenyl]-2,2'-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: methyl 2-iodo-3-methylbenzoate With isopropylmagnesium chloride In tetrahydrofuran at -30℃; for 0.5h; Inert atmosphere; Stage #2: With dilithium tetrachlorocuprate(II); oxygen In tetrahydrofuran at 20℃; for 2h;
  • 30
  • [ 16419-60-6 ]
  • [ 103441-60-7 ]
  • [ 1433988-26-1 ]
YieldReaction ConditionsOperation in experiment
With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In tetrahydrofuran; water at 60℃; Inert atmosphere;
  • 31
  • [ 103441-60-7 ]
  • [ 153435-63-3 ]
  • [ 1445596-17-7 ]
YieldReaction ConditionsOperation in experiment
150 mg With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 130℃; for 0.25h; Microwave irradiation; 59 Description 59: methyl 3-methyl-2-(pyrim idin-2-yl)benzoate (D59) (D58) (353mg, 1.3mmol) was dissolved dry DMF (3m1), then CsF (4lOmg,2.7mmol), Cul (27mg, 0.l4mmol), [Ph3P]4Pd (153mg, 0.l3mmol) and pyrimidine-2-tributylstannane (528mg, 1.43mmol; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) were added. The mixture was warmed at 130°C for 15 minutes (microwave), then poured in aqueous saturated solution of NH4CI and extracted with AcOEt (3x50m1). The organiclayers were combined, dried (Na2SO4) and concentrated under vacuum; the crude mixture was purified by silica gel column chromatography (cyclohexane to cyclohexane/AcOEt=1/1) to give 150mg of the title compound as yellow oil.MS (ESI) mlz: 229[M+H].1H NMR (CDCl3) 5 ppm = 8.87 (d, J = 4.9 Hz, 1 H), 7.91 (d, J = 7.3 Hz, 1 H), 7.56 - 7.46(m, 1 H), 7.43 (d, J = 7.8 Hz, 1 H), 7.34 - 7.21 (m, 2H, under the solvent peak), 2.18 (s, 3H).
150 mg With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 130℃; for 0.25h; Microwave irradiation; 59 methyl 3-methyl-2-(pyrimidin-2-yl)benzoate (D59) (D58) (353 mg, 1.3 mmol) was dissolved dry DMF (3 ml), then CsF (410 mg, 2.7 mmol), CuI (27 mg, 0.14 mmol), [Ph3P]4Pd (153 mg, 0.13 mmol) and pyrimidine-2-tributylstannane (528 mg, 1.43 mmol; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) were added. The mixture was warmed at 130° C. for 15 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt (3×50 ml). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; the crude mixture was purified by silica gel column chromatography (cyclohexane to cyclohexane/AcOEt=1/1) to give 150 mg of the title compound as yellow oil. MS (ESI) m/z: 229[M+H]+. 1H NMR (CDCl3) δ ppm=8.87 (d, J=4.9 Hz, 1H), 7.91 (d, J=7.3 Hz, 1H), 7.56-7.46 (m, 1H), 7.43 (d, J=7.8 Hz, 1H), 7.34-7.21 (m, 2H, under the solvent peak), 2.18 (s, 3H).
  • 32
  • [ 5471-82-9 ]
  • [ 103441-60-7 ]
  • 33
  • [ 103441-60-7 ]
  • [ 5176-28-3 ]
  • 10-methyl-13,14-cis-dihydrobenzo[c]phenanthridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride; zinc In 1,4-dioxane at 100℃; for 1h; Inert atmosphere;
  • 34
  • [ 106-41-2 ]
  • [ 103441-60-7 ]
  • C15H13BrO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With copper(l) iodide; caesium carbonate In toluene for 10h; Inert atmosphere; Reflux;
  • 35
  • [ 103441-60-7 ]
  • [ 106-48-9 ]
  • C15H13ClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With copper(l) iodide; caesium carbonate In toluene for 10h; Inert atmosphere; Reflux;
  • 36
  • [ 103441-60-7 ]
  • [ 536-74-3 ]
  • methyl 3-methyl-2-(2-phenylethynyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
760 mg Stage #1: methyl 2-iodo-3-methylbenzoate With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: 1-ethynylbenzene In N,N-dimethyl-formamide at 80 - 85℃; for 15h; Inert atmosphere;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; Inert atmosphere; Schlenk technique;
  • 37
  • [ 103441-60-7 ]
  • [ 80077-72-1 ]
  • [ 1369842-38-5 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: diethyl difluoro(trimethylsilyl)methylphosphonate With cesium fluoride; copper(l) chloride In N,N-dimethyl-formamide; acetonitrile at 0 - 40℃; for 2h; Glovebox; Sealed tube; Inert atmosphere; Stage #2: methyl 2-iodo-3-methylbenzoate With 1,10-Phenanthroline In N,N-dimethyl-formamide; acetonitrile at 20℃; for 16h; Glovebox; Sealed tube; Inert atmosphere;
  • 38
  • diisopropyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate [ No CAS ]
  • [ 103441-60-7 ]
  • diisopropyl 1-((3S,3aR,8aS)-4-(methoxycarbonyl)-3,3a,8,8atetrahydrocyclopenta[a]inden-3-yl)hydrazine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl-ammonium chloride; cesium acetate In toluene at 80℃; for 12h; Schlenk technique; Inert atmosphere;
  • 39
  • C13H18N2O4 [ No CAS ]
  • [ 103441-60-7 ]
  • diethyl 1-((3S,3aR,8aS)-4-(methoxycarbonyl)-2-vinyl-3,3a,8,8a-tetrahydrocyclopenta[a]inden-3-yl)hydrazine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl-ammonium chloride; cesium acetate In toluene at 80℃; for 12h; Schlenk technique; Inert atmosphere;
  • 40
  • C15H22N2O4 [ No CAS ]
  • [ 103441-60-7 ]
  • diisopropyl 1-((3S,3aS,8aR)-4-(methoxycarbonyl)-2-vinyl-3,3a,8,8a-tetrahydrocyclopenta[a]inden-3-yl)hydrazine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl-ammonium chloride; cesium acetate In toluene at 80℃; for 12h; Schlenk technique; Inert atmosphere;
  • 41
  • [ 1559-02-0 ]
  • [ 103441-60-7 ]
  • diethyl 2-(2-(methoxycarbonyl)-6-methylphenethyl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: methyl 2-iodo-3-methylbenzoate With TurboGrignard In tetrahydrofuran; 2-methyltetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: diethyl cyclopropane-1,1-dicarboxylate With 1,3-dimethyl-2-imidazolidinone; copper(I) iodide dimethyl sulfide complex In tetrahydrofuran; 2-methyltetrahydrofuran at -78 - 23℃; Inert atmosphere; Sealed tube;
  • 42
  • [ 1493-13-6 ]
  • [ 103441-60-7 ]
  • [ 71-43-2 ]
  • C16H14F3IO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 80℃; for 8h;
  • 43
  • [ 1455-20-5 ]
  • [ 103441-60-7 ]
  • [ 292638-85-8 ]
  • C21H24O4S [ No CAS ]
  • 44
  • [ 87199-17-5 ]
  • [ 103441-60-7 ]
  • methyl 4'-formyl-6-methyl-[1,1'-biphenyl]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 65 - 80℃; Inert atmosphere;
  • 45
  • [ 103441-60-7 ]
  • 5-methoxyl-2-isocyano-N-propylbenzamide [ No CAS ]
  • (S)-methyl 2-(6-methoxy-4-oxo-3-propyl-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 46
  • [ 103441-60-7 ]
  • 2-isocyano-N-(3-phenylpropyl)benzamide [ No CAS ]
  • (S)-methyl 3-methyl-2-(4-oxo-3-(3-phenylpropyl)-3,4-dihydroquinazolin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 47
  • [ 870672-32-5 ]
  • [ 103441-60-7 ]
  • (S)-methyl 3-methyl-2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 48
  • [ 103441-60-7 ]
  • N-ethyl-2-isocyanobenzamide [ No CAS ]
  • (S)-methyl 2-(3-ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 49
  • N-benzyl-2-isocyanobenzamide [ No CAS ]
  • [ 103441-60-7 ]
  • (S)-methyl 2-(3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 50
  • [ 103441-60-7 ]
  • 4-chloro-2-isocyano-N-propylbenzamide [ No CAS ]
  • (S)-methyl 2-(7-chloro-4-oxo-3-propyl-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 51
  • [ 103441-60-7 ]
  • 5-chloro-2-isocyano-N-propylbenzamide [ No CAS ]
  • (S)-methyl 2-(6-chloro-4-oxo-3-propyl-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 52
  • [ 870672-10-9 ]
  • [ 103441-60-7 ]
  • (S)-methyl 2-(3-butyl-4-oxo-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 53
  • [ 103441-60-7 ]
  • 5-bromo-2-isocyano-N-propylbenzamide [ No CAS ]
  • (S)-methyl 2-(6-bromo-4-oxo-3-propyl-3,4-dihydroquinazolin-2-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With palladium diacetate; C23H28NO2P; caesium carbonate; Trimethylacetic acid In toluene at 60℃; for 1h; Schlenk technique; Inert atmosphere; enantioselective reaction;
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 103441-60-7 ]

Aryls

Chemical Structure| 610-97-9

[ 610-97-9 ]

Methyl 2-iodobenzoate

Similarity: 1.00

Chemical Structure| 14192-13-3

[ 14192-13-3 ]

Methyl 2,5-diiodobenzoate

Similarity: 1.00

Chemical Structure| 1048025-64-4

[ 1048025-64-4 ]

2-Iodo-5-(methoxycarbonyl)benzoic acid

Similarity: 1.00

Chemical Structure| 1427082-89-0

[ 1427082-89-0 ]

4-Iodo-3-(methoxycarbonyl)benzoic acid

Similarity: 1.00

Chemical Structure| 165534-79-2

[ 165534-79-2 ]

Dimethyl 2-iodoterephthalate

Similarity: 1.00

Esters

Chemical Structure| 103440-52-4

[ 103440-52-4 ]

Methyl 2-Iodo-5-methylbenzoate

Similarity: 1.00

Chemical Structure| 14192-13-3

[ 14192-13-3 ]

Methyl 2,5-diiodobenzoate

Similarity: 1.00

Chemical Structure| 1048025-64-4

[ 1048025-64-4 ]

2-Iodo-5-(methoxycarbonyl)benzoic acid

Similarity: 1.00

Chemical Structure| 1427082-89-0

[ 1427082-89-0 ]

4-Iodo-3-(methoxycarbonyl)benzoic acid

Similarity: 1.00

Chemical Structure| 165534-79-2

[ 165534-79-2 ]

Dimethyl 2-iodoterephthalate

Similarity: 1.00

Iodides

Chemical Structure| 610-97-9

[ 610-97-9 ]

Methyl 2-iodobenzoate

Similarity: 1.00

Chemical Structure| 14192-13-3

[ 14192-13-3 ]

Methyl 2,5-diiodobenzoate

Similarity: 1.00

Chemical Structure| 1048025-64-4

[ 1048025-64-4 ]

2-Iodo-5-(methoxycarbonyl)benzoic acid

Similarity: 1.00

Chemical Structure| 1427082-89-0

[ 1427082-89-0 ]

4-Iodo-3-(methoxycarbonyl)benzoic acid

Similarity: 1.00

Chemical Structure| 165534-79-2

[ 165534-79-2 ]

Dimethyl 2-iodoterephthalate

Similarity: 1.00