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CAS No. : | 18282-40-1 | MDL No. : | MFCD00040871 |
Formula : | C8H9I | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZEJZDNMOGNUIHL-UHFFFAOYSA-N |
M.W : | 232.06 | Pubchem ID : | 140367 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.93 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
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) : | -5.0 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 3.82 |
Log Po/w (WLOGP) : | 2.85 |
Log Po/w (MLOGP) : | 3.83 |
Log Po/w (SILICOS-IT) : | 3.61 |
Consensus Log Po/w : | 3.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.11 |
Solubility : | 0.0179 mg/ml ; 0.0000771 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.52 |
Solubility : | 0.0709 mg/ml ; 0.000305 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.15 |
Solubility : | 0.0166 mg/ml ; 0.0000714 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.44 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: ortho-ethylaniline With sulfuric acid; sodium nitrite In water at -20℃; for 1h; Stage #2: With potassium iodide In water at 20℃; for 18h; | 14 2-Ethyl-iodobenzene With mechanical stirring, a suspension of 75 2-ethylaniline (36.4 g, 0.30 mol) in 25 wt % 76 sulfuric acid (240 mL), was cooled in 1, 2-xylene-dry ice bath to -20° C. 77 Sodium nitrite (21 g, 0.30 mol) in 10 water (40 mL) was added, and after 1 hour at this temperature, the gelly mass was transferred to a solution of 14 potassium iodide (150 g, 0.90 mol) in water (150 mL), and the mixture was left stirring at room temperature for 18 hours. The reaction 78 mass was extracted into hexanes and the extract after drying was passed through a column of silica gel to get the product as a colorless oil after evaporation of the solvent, 59.14 g (85%). Mass spec: m/z 232 (M+). Anal. Calcd. for C8H9I: C, 41.41; H, 3.91 and I, 54.32%. Found: C, 41.50; H, 3.90 and I, 54.28%. 1H NMR (CDCl3) δ ppm: 1.20 (t, 3H, 7.52 Hz), 2.73 (q, 2H, 7.52 Hz), 6.86 (td, 1H, 7.50 and 1.76 Hz), 7.25 (m, 2H), 7.80 (dd, 1H, 0.88 and 7.88 Hz). |
With hydrogenchloride; potassium iodide; sodium nitrite | ||
With sulfuric acid; potassium iodide; sodium nitrite |
95 %Chromat. | Stage #1: ortho-ethylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.00277778h; Stage #2: With potassium iodide In water at 0 - 5℃; for 2h; | 2 Example 2 In the reaction apparatus shown in Fig. 1,Sodium nitrite solution andO-ethylaniline at 1.44 ml / min,1 ml / min(Molar ratio of sodium nitrite to o-ethylaniline 1.05: 1)C feed tubeWas injected into the first micro-mixer 1 (internal cross-finger micro mixer, SIMM-V2, IMM, Germany, mixed channel inner diameter 45 m)The mixed solution was then passed through a first microchannel a (inner diameter: 0.3 mm, residence time 0.5 s)Into the second micro mixer 2 (inner diameter 5 mm)The hydrochloric acid injected from the feed line A was mixed with hydrochloric acid at a flow rate of 4 ml / min (the molar ratio of hydrochloric acid to o-ethylaniline: 3.2: 1) in a constant temperature reaction bath T1 (0C)And then into the second micro-channel b (ID: 1mm) to continue the reaction 10s,The diazonium salt solution was collected with a round bottom flask E charged with potassium iodide,The flask E was stirred for 2 h in a constant temperature reaction bath T2 (0 to 5 ° C)The organic phase is post-GC analysis of o-ethyl aniline conversion was 97%The yield of o-ethyl iodobenzene was 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With norborn-2-ene; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; | |
92% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 0.0833333h; Microwave irradiation; | 3.2. General Procedure for the Sonogashira CouplingReaction General procedure: Aryl halide (1.5 mmol), alkyne (1.8 mmol, 1.2 equiv),Pd(PPh3)2Cl2 (53 mg, 0.075 mmol, 0.05 equiv) and Et3N(666 mg, 6 mmol, 4 equiv) were added to 10 mL microwave vial containing 4 mL [BMIm][BF4]. The mixture was irradiatedin a microwave reactor at 80 °C for 5 minutes. Completionof the reaction was confirmed by TLC. Then the mixturewas extracted with hexane (4 x 10 mL) and the organic layerswere combined. The solvent was removed by an evaporatorand the residue was purified by flash column chromatographyto afford the corresponding product. The ionic liquidcontaining catalyst was washed with water (3 x 5mL) thenwas placed in a high vacuo system to remove water residue.The ionic liquid was used for the next cycle without furtherpurification. |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In 1,4-dioxane at 45℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 2h; atmospheric pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: dicyclohexylphosphane With copper(l) iodide; N,N`-dimethylethylenediamine In toluene Stage #2: 1-ethyl-2-iodobenzene With caesium carbonate In toluene at 110℃; for 12h; Stage #3: With borane In tetrahydrofuran; toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 87% 2: 6% 3: 3% | With potassium carbonate In N,N-dimethyl-formamide at 105℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 76% 2: 4% 3: 9% | Stage #1: norborn-2-ene; oct-1-ene; 1-ethyl-2-iodobenzene With potassium carbonate In N,N-dimethyl-formamide at 105℃; for 16h; Stage #2: With hydrogen In ethyl acetate at 20℃; for 48h; atmospheric pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 79% 2: 9% 3: 4% | With potassium carbonate In N,N-dimethyl-formamide at 105℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 79% 2: 4% 3: 1% | With potassium carbonate In N,N-dimethyl-formamide at 105℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 90% 2: 4% | With copper(l) iodide; diethylamine at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With norborn-2-ene; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; | |
64% | With norborn-2-ene; potassium carbonate In N,N-dimethyl-formamide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 168h; | |
79% | With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 168h; | |
93% | With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: 1-ethyl-2-iodobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (R)-Carvone In tetrahydrofuran; hexane at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With caesium carbonate In acetonitrile at 70℃; for 144h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In hexane; toluene | 5 Synthesis of Compound 5.01 A degassed (3* freeze-thaw cycles) mixture of 1.00 mL 1-ethyl-2-iodo-benzene (6.97 mmol, 1.00 equiv), 3.47 g 4-ethoxyphenylboronic acid (20.9 mmol, 3.00 equiv), and 402 mg tetrakis(triphenylphosphine)palladium(0) (0.349 mmol, 0.0501 equiv) was dissolved in 8.0 mL toluene and 8.0 mL aqueous 2M sodium carbonate solution and the biphasic mixture heated to 100° C. (external temperature, oil bath). After 16 h the reaction was cooled to room temperature and the organic phase separated. The aqueous layer was extracted with 50% ethyl acetate in hexane (2*25 mL) and the combined organic separations dried over magnesium sulfate, filtered, and concentrated in vacuo to yield a yellow oil. The crude material was purified by column chromatography on silica gel (3.5 cm o.d.*20 cm h) eluding with 5% ethyl acetate in hexane. Fractions containing product at Rf=0.68, 10% ethyl acetate in hexane, were combined and concentrated in vacuo to afford 1.54 g product, including impurity, as a colorless oil; ca. 1.23 g pure product. An impurity of ca. 20%, identified as the homocoupling product 4,4'-diethoxybiphenyl and quantified by relative ratio of integrated 1H NMR resonance signals, was carried forward with the product to the next step. 1H NMR (CDCl3) δ1.15 (t, 3H, J=7.6 Hz), 1.49 (t, 3H, J=7.2 Hz), 2.65 (q, 2H, J=7.6 Hz), 4.12 (q, 2H, J=7.2 Hz), 6.98 (d, 2H, J=8.4 Hz), 7.22-7.28 (m, 2H), 7.27 (d, 2H, J=8.4 Hz), 7.31-7.34 (m, 2H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride In toluene | 16 Preparation of Fmoc-(D,L)-5-ethyl-2 aminotetraline-2-carboxylic acid (Fmoc-(D,L) 5-EtAtc-OH) EXAMPLE 16 Preparation of Fmoc-(D,L)-5-ethyl-2 aminotetraline-2-carboxylic acid (Fmoc-(D,L) 5-EtAtc-OH) A mixture of 3-(2-ethylphenyl)propanoic acid (prepared in 3 steps from 1-ethyl-2-iodobenzene, 4.24 g, 23.8 mmole), thionyl chloride (9.50 ml, 130 mmol) and toluene (100 ml) was refluxed for 2 hours. Concentration in vacuo gave 3-(2-ethylphenyl)propanoyl chloride which was taken up in methylene chloride and used in the next step as a crude. | |
With thionyl chloride In toluene | 15.1 Step 1 Step 1 A mixture of 3-(2-ethylphenyl)propanoic acid (prepared in 3 steps from 1-ethyl-2-iodobenzene, 4.24 g, 23.8 mmole), thionyl chloride (9.50 ml, 130 mmole) and toluene (100 ml) was refluxed for 2 hours. Concentration in vacuo gave 3-(2-ethylphenyl)propanoyl chloride which was taken up in methylene chloride and used in the next step as a crude. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: 4-methyl-6-oxo-2-{2-[(phenylmethyl)oxy]phenyl}-1,6-dihydro-5-pyrimidinecarbonitrile With sodium hydroxide In ethanol; water Stage #2: 1-ethyl-2-iodobenzene for 27h; Heating / reflux; | 148.c To a solution of 4-methyl-6-oxo-2-{2-[(phenylmethyl)oxy]phenyl}-1 ,6-dihydro-5- pyrimidinecarbonitrile (0.265 g, 0.836 mmol) in ethanol:H20 (95:5, 5.6 ml_) was added sodium hydroxide (0.193 g, 4.83 mmol). After the complete dissolution of 4-methyl-6-oxo-2~{2- [(phenylmethyl)oxy]phenyi}-1 ,6~dihydro-5-pyrimidinecarbonitrile, 2-iodoethylbenzene (2.5 mL, 17.3 mmol) was added. The reaction flask was sealed and heated at reflux for 27 h. The reaction mixture was cooled to room temperature and poured into cold H2O. The resulting aqueous layer was extracted five times with CH2Cl2- The combined organic layers were washed with sat. Na2S2Oa. and brine, dried over Na2SO4, filtered, and concentrated. Column chromatography (0-2% CH3OH/CH2CI2) afforded 0.117 g (33%) of the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.45 (m, 1 H), 7.30 (m, 3H), 7.18 (m, 5H), 7.05 (m, 2H), 6.95 (m, 1 H), 6.75 (m, 2H), 5.1 (dd, 2H), 4.40 (m, 1 H), 3.72 (m, 1H), 2.84 (m, 1H), 2.76 (m, 1 H), 2.58 (s, 3H); MS(ESI) 422.2 (M + H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With norbornene; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With norborn-2-ene; potassium phenolate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 23℃; Inert atmosphere; | |
87% | Stage #1: 1-ethyl-2-iodobenzene; propargyl alcohol With trans-bis(triphenylphosphine)palladium dichloride; diethylamine at 20℃; for 0.25h; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 3h; Inert atmosphere; | |
Stage #1: 1-ethyl-2-iodobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.166667h; Inert atmosphere; Stage #2: propargyl alcohol Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 1-ethyl-2-iodobenzene; 2-bromobenzylamine With norborn-2-ene; palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 130℃; Inert atmosphere; Stage #2: With oxygen In N,N-dimethyl-formamide at 130℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl acetamide at 140℃; for 18h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl acetamide at 140℃; for 18h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl acetamide at 140℃; for 18h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With 1,3-bis-(diphenylphosphino)propane; water; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20 - 115℃; for 6h; Inert atmosphere; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In tetrahydrofuran; toluene at 110℃; for 24h; Inert atmosphere; | |
86% | In tetrahydrofuran; toluene at 80℃; for 48h; Schlenk technique; Inert atmosphere; | Coupling Reaction of Arylmagnesium Bromides with Aryl Iodides (Table 4): GeneralProcedure. General procedure: An aryl iodide (2': 0.20 mmol) in a 20 mL Schlenk tube was added successively toluene (1.5 mL), a THF solution of an arylmagnesium bromide (1: 0.30 mmol) and THF (overall 0.50 mL), and the resulting mixture was stirred at 80 °C for 24 h. After cooling, the reaction mixture was quenched with a 1 N HCl aqueous solution (1.0 mL) and extracted with Et2O (10 mL x 3). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to silica gel chromatography (hexane orhexane/diethyl ether, PTLC) to give the corresponding coupling product (3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With [RhCl2(p-cymene)]2; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Air atmosphere; regioselective reaction; | |
77% | With copper(l) iodide; 1,10-Phenanthroline; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 140℃; for 24h; Air atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 28% 2: 18% 3: 16% | With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 24h; Schlenk technique; Inert atmosphere; | 19 4.2 General procedure for the reaction of ortho-substituted aryl iodides with 2-bromophenols and norbornene A Schlenk-type flask, equipped with a magnetic stirring bar, was charged under nitrogen with K2CO3 (246 mg, 1.78 mmol) and with a DMF solution (5 mL) of Pd(OAc)2 (5 mg, 0.022 mmol). A DMF solution (5 mL) of the ortho-substituted aryl iodide (0.56 mmol), the 2-bromophenol (0.56 mmol), and norbornene (63 mg, 0.67 mmol) or norbornadiene (123 mg, 1.34 mmol) was then added. The resulting mixture was stirred in an oil bath at 105 °C for 24-66 h. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL) and washed with a saturated solution of NaCl (3×25 mL). The organic layer was dried over anhydrous Na2SO4, the solvent was removed under reduced pressure and the products were isolated by flash column chromatography on silica gel using mixtures of hexane-EtOAc as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ammonium hydroxide; 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane; palladium diacetate In toluene at 130℃; Autoclave; | General procedure for Palladium-Catalyzed Aminocarbonylation of Aryl Iodides Using Aqueous Ammonia: General procedure: To a 45 mL glass-lined autoclave, 1 (0.5 mmol), Pd(OAc)2 (0.01mmol), CYTOP292 (0.02mmol), aqueous ammonia (0.2 mL) and toluene (10 mL) were sequentially added. After sealing, the autoclave was purged three times with carbon monoxide and pressurized with 100 psi of CO. The resulting mixture was then heated at 100 °C for 20 h. The autoclave was removed from the oil bath and cooled to room temperature prior to the release of excess carbon monoxide. The reaction mixture was concentrated by rotary evaporator, and purified by flash chromatography on silica gel with a mixture of hexanes and ethyl acetate (2:1to 1:2) as the eluent to afford the products. |
45% | With 1H-imidazole; ammonium carbamate; triethylamine In N,N-dimethyl-formamide at 130℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide In 1-methyl-pyrrolidin-2-one at 180℃; for 4h; Microwave irradiation; | 157 Example 157I -(2-ethylphenyl)-4-[4-(2-methoxyphenyl)piperazin- I -yI]-1 H-pyrazolo[3,4- d]pyrimidine Example 157I -(2-ethylphenyl)-4-[4-(2-methoxyphenyl)piperazin- I -yI]-1 H-pyrazolo[3,4- d]pyrimidine 100 mg (0.32 mmo[) 4-[4-(2-methoxypheny[)piperazin-1 -y[]-1 H-pyrazo[o[3,4- d]pyrimidine, 112.2 mg (0.48 mmo[) 1-ethy[-2-iodobenzene, 18.4 mg (0.10 mmo[) copper(I) iodide, 144 mg (0.68 mmo[) tripotassium phosphate and 27.5 mg (0.19 mmo[) trans-N,N’-dimethy[cyc[ohexane-1,2-diamine in 3 mL anhydrous NMP wereheated under microwave irradiation 4 h at 180CC. The reaction mixture was poured into water and extracted three times with ethy[ acetate. The combined organic phases were washed with 0.5 M aqueous EDTA so[ution and three times with water, dried over magnesium su[fate and concentrated. The residue was purified by HPLC affording 11 mg (8%) product.LC-MS (ana[ytica[ method 3): R = 1.45 mm, MS (ESipos): mlz = 415 (M+H).1H-NMR (400MHz, DMSO-d6): 6 [ppm]= 0.93 (t, 3H), 2.38 (d, 2H), 3.10 - 3.18 (m, 4H),3.83 (5, 3H), 4.08 - 4.17 (m, 4H), 6.85 - 7.04 (m, 4H), 7.32 (5, 1H), 7.35 - 7.40 (m,1H), 7.43 - 7.51 (m, 2H), 8.25 (5, 1H), 8.59 (5, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With copper(I) oxide; potassium carbonate In N,N-dimethyl-formamide for 72h; Reflux; | General procedure for preparation of compounds 2a-2n General procedure: A suspension of indole-3-carbaldehyde 1 (0.411 g, 2.8 mmol),Cu2O (0.3 equiv), K2CO3 (2.0 equiv) and aryl halide (2.0 equiv) inanhydrous DMF (5.6 mL) was refluxed for 72 h. After cooling to RT,the reaction mixture was filtrated over a celite pad eluting withEtOAc. Solvents were removed and the residue dissolved in EtOAc(20 mL) washed successively by 2.5% aqueous NH4OH, 1 M HCl andsaturated aqueous NaCl. The organic phase was dried over Na2SO4,filtered and concentrated. The residue was purified by flash columnchromatography on silica gel (PE/EtOAc 9:1 to 7:3) to furnish thedesired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78 - 30℃; for 1h; Inert atmosphere; | 1-33 <Preparation of the Compound of the Formula 31-1> Under nitrogen atmosphere, at 0° C., to tetramethylethylenediamine 3.2 ml was added n-butyllithium 16 ml (1.6M hexane solution) and the resulting mixtures were stirred for 10 minutes. Thereafter, at 0° C. under ice-cooling, thereto was added the compound of the formula (32-1) 5 g. Thereafter, the resulting solutions were cooled to -78° C. and then thereto was added a suspension of trichlorobismuth 2.3 g in tetrahydrofuran 15 ml and the resulting mixtures were stirred for 1 hour with heating to rt. Thereafter, to the resulting reaction solutions was added water 20 ml and the aqueous layers were extracted with chloroform. The resulting chloroform layers were washed with saturated saline, dried over anhydrous sodium sulfate and filtered, and the resulting filtrates were concentrated under reduced pressure to give the compound of the formula (33-1) 2.6 g as crude products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate In acetonitrile at 85℃; for 6h; Inert atmosphere; | 4-Ethyl-5-methyl-8,9-dimethoxyphenanthridin-6(5H)-one (6) A flask was charged under nitrogen with Pd(OAc)2 (3.0 mg, 0.013 mmol),tri-2-furylphosphine (6.2 mg, 0.027 mmol), K2CO3 (72.3 mg, 0.52mmol), the amide 4 (0.26 mmol), a solution of norbornene (26.9 mg,0.286 mmol) in anhydrous solvent (5.8 mL), and 1-ethyl-2-iodobenzene(5, 0.26 mmol). The reaction mixture was heated with stirring at 85°C for 6 h and then cooled to room temperature. After the addition ofsaturated NH4Cl (30 mL) and extraction with EtOAc (3×15 mL), thecombined organic extracts were washed with brine (30 mL) and driedover Na2SO4. Removal of the solvent under reduced pressure gave thecrude product, which was purified by flash chromatography on silicagel to furnish 6 as white wax (58 mg, 75% yield). IR (KBr) nmax 3446,2923, 1642, 1550, 1512, 1464, 1360, 1029, 691, 563, cm-1; 1H NMRδ 8.21 (d, J = 7.6 Hz, 1H), 7.71 (s, 1H), 7.60 (s, 1H), 7.32 (d, J = 7.4Hz, 1H), 7.29-7.25 (m, 1H), 3.92 (s, 3H), 3.89 (s, 3H), 3.76 (s, 3H),3.01-3.03 (m, 2H), 1.25 (t, J = 8.1 Hz, 3H); 13C NMR: δ 166.1, 139.4,134.5, 132.5, 132.1, 131.3, 128.7, 127.5, 125.1, 129.6, 122.2, 121.1, 121.0,58.3, 58.1, 38.6, 28.1, 15.5; HREIMS m/z 297.1361 [M]+ (calcd forC18H19NO3, 297.1365). |
75% | With norborn-2-ene; palladium diacetate; potassium carbonate In water; acetonitrile at 85℃; for 6h; Inert atmosphere; | 2.3 Synthesis of Specific Compounds (3) 4-ethyl-5-methyl-5H-8,9-dimethoxyphenanthridin-6-one (15): under nitrogen atmosphere, palladium acetate (3.0 mg, 0.013 mmol), TFPA (6.2 mg, 0.027 mmol), anhydrous potassium carbonate (72.3 mg, 0.52 mmol), compound 4 (0.1 mmol), and 2-ethyl-iodobenzene (0.26 mmol) were added to a round bottom flask, and anhydrous acetonitrile was added to dissolve the above mixture. An aqueous solution containing norbornene (26.9 mg, 0.286 mmol) was added, and the resultant reaction mixture was stirred for 6 hours at 85° C. then cooled to room temperature. The reaction mixture was quenched with saturated ammonium chlorine (30 mL), and extracted with ethyl acetate (3*15 ml). The organic layer was dried with anhydrous sodium sulfate, and then concentrated. The obtained residue was purified by column chromatography to give compound 15 (22.5 mg, yield: 75%). |
75% | With norborn-2-ene; palladium diacetate; potassium carbonate In acetonitrile at 85℃; for 6h; Inert atmosphere; | 3 4-ethyl-5-methyl-5H-8,9-dimethoxyphenanthridin-6-one (15): Preparation of Example 3 4-ethyl-5-methyl-5H-8,9-dimethoxyphenanthridin-6-one (15): Under nitrogen protection, palladium acetate (3.0 mg, 0.013 mmol), TFPA (6.2 mg, 0.027 mmol), anhydrous potassium carbonate (72.3 mg, 0.52 mmol), compound 4 (0.1 mmol) and 2-ethyl iodobenzene (0.26 mmol) were added into a round bottom flask, anhydrous acetonitrile was added to dissolve, then added to an aqueous flask containing norbornene (26.9 mg, 0.286 mmol) and stirred at 85 °C for 6 hours. After the reaction was completed, cooled to room temperature, saturated ammonium chloride (30 mL) was added and extracted with ethyl acetate (3 * 15 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography to obtain compound 15 (22.5 mg, yield: 75%). |
With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 8h; Inert atmosphere; | Synthesis of intermediates 1a-1e By referencing the synthesis method of 6-Phenanthridinones2, amide substrates werecoupled to 1-iodo-2-ethylbenzene or 1-iodo-2-methylbenzene to afford compound1a-1e. A flask was charged under nitrogen with Pd(OAc)2 (0.5 mmol), tri(2-furyl)phosphine (1.1 mmol), K2CO3 (20 mmol), the amides 1-5 (10 mmol), a solution ofnorbornene (12 mmol) in anhydrous DMF (20 mL), and 1-iodo-2-methylbenzene or1-iodo-2-ethylbenzene(11 mmol). The reaction mixture was heated with stirring at105 °C for 8 h and then cooled to r.t. After the addition of saturated NH4Cl (50 mL)and extraction with EtOAc (3×50 mL), the combined organic extracts were washed with brine (30 mL) and dried over Na2SO4. Removal of the solvent under reducedpressure gave the crude product, which was purified by flash chromatography onsilica gel to furnish 1a-1e as a colorless solid. (yield 75-85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bismuth(III) chloride; n-butyllithium; 1,4-diaminobutane In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; | 1-33 Production Example 1-33 Production of Compound Represented by Formula (1-97) Production of Compound Represented by Formula 31-1 16 ml of n-butyllithium (1.6M hexane solution) was added to 3.2 ml of tetramethylenediamine at 0° C. in a nitrogen atmosphere, followed by stirring for 10 minutes. Next, 5 g of the compound represented by Formula (32-1) was added thereto at 0° C. under ice-cooling. Next, the obtained solution was cooled to -78° C., a suspension of 2.3 g of trichlorobismuth in 15 ml of tetrahydrofuran was added thereto, followed by stirring for 1 hour while heating to room temperature. Next, 20 ml of water was added to the obtained reaction liquid, and the aqueous layer was extracted with chloroform. The obtained chloroform layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and filtered, and the obtained filtrate was concentrated under reduced pressure, whereby 2.6 g of a crude product of the compound represented by Formula (33-1) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With carbon disulfide; cycl-isopropylidene malonate; triethylamine; copper(l) chloride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | Conversion of aryl iodides into diaryl disulfides using Meldrum’s acid dithioate General procedure: A mixture of Meldrum’s acid (1 mmol) and Et3N (2 mmol) in DMF was stirred for 15 min at r.t. Then, CS2 (1 mmol) was added and stirred for 15 min. Then, the obtained mixture was added to a stirred solution of aryl halide (1 mmol) and CuCl (0.1 mmol) in DMF (2 ml), and heated at 100 C for 4h. When the reaction was completed (TLC), the mixture was extracted with CH2Cl2 (3 3ml) and H2O (3ml). The organic layer was separated and dried (Na2SO4) and the solvent was evaporated in vacuo to give the diaryl disulfide. The product was purified by column chromatography on silica gel (EtOAc / Petroleum ether, 1:4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: 1-ethyl-2-iodobenzene With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water In acetonitrile at 80℃; for 8h; Stage #2: With ammonium hydroxide; iodine In acetonitrile at 60℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With norbornene; palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
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90% | With norborn-2-ene; palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 100℃; for 14.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 60℃; for 18h; | |
65% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 60℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium fluoride; palladium diacetate; silver carbonate at 110℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium fluoride; palladium diacetate; silver carbonate at 110℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: ethyl 3-(1H-indol-3-yl)-2-isocyanopropanoate; 1-ethyl-2-iodobenzene With palladium diacetate; triphenylphosphine; cesium pivalate In toluene at 80℃; for 5h; Inert atmosphere; Stage #2: In toluene at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere; | |
72% | With C19H25CuN5(1+)*F6P(1-); potassium carbonate In N,N-dimethyl-formamide at 135 - 140℃; Sealed tube; | 4.4 Cu-catalyzed coupling of aryl iodide and phenylacetylene derivatives General procedure: A 20mL scintillation vial was charged with a Teflon stir bar, copper complex (0.1mmol), 76 potassium carbonate (0.75mmol), aryl iodide (0.5mmol), 77 phenylacetylene (0.75mmol) in 5mL non-anhydrous DMF in air. The vial was sealed and placed in an oil bath with pre-adjusted temperature at 135-140°C. After the allowed time, the reaction mixture was cooled down, diluted with 25-30mL ethyl acetate, and filtered through a pad of silica gel. The solvent was then removed under vacuum and the residue was purified by column chromatography using mixtures of hexane and ethyl acetate to obtain analytically pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; 5-carboxybicyclo<2.2.1>hept-2-ene; XPhos In acetonitrile at 70℃; chemoselective reaction; | |
73% | With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; 5-norbornene-endo-2-carboxylic acid; XPhos In acetonitrile at 70℃; Inert atmosphere; Schlenk technique; | General procedure for the synthesis of compounds 3 General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70°C and stirred for 5-24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; 5-carboxybicyclo<2.2.1>hept-2-ene; XPhos In acetonitrile at 70℃; chemoselective reaction; | |
50% | With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; 5-norbornene-endo-2-carboxylic acid; XPhos In acetonitrile at 70℃; Inert atmosphere; Schlenk technique; | General procedure for the synthesis of compounds 3 General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70°C and stirred for 5-24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With norborn-2-ene; bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; p-benzoquinone In dimethyl sulfoxide at 140℃; for 3h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 4-bromobenzenecarbonitrile; 1-ethyl-2-iodobenzene With norbornene; tetrabutylammonium acetate; palladium diacetate; XPhos In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ethene In N,N-dimethyl-formamide at 115℃; for 3h; Inert atmosphere; Flow reactor; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 18-crown-6 ether; copper; potassium carbonate at 240 - 270℃; for 18h; Inert atmosphere; | 15 [N,7-(Benzothiazol-2-yl)-9,9-diethylfluoren-2-yl)-N-(2,6-diethylphenyl)-N-(2-ethylphenyl)amine (AF337-21) A mixture of 78 2-ethyl iodobenzene (6.09 g, 25.9 mmol), 69 N,7-[(benzothiazol-2-yl)-9,9-diethylfluoren-2-yl]-N-(2,6-diethylphenyl)amine (Example 12; (2 g, 3.98 mmol), 60 copper powder (0.39 g, 6.14 mmol), 18-crown-6 (0.105 g, 0.397 mmol) and 59 potassium carbonate (2.4 g, 17.4 mmol) was kept in a heating bath at 240-270° C. under nitrogen for 18 hours, cooled, diluted with toluene and filtered. The 22 toluene solution was washed with water, dried and concentrated. The residue (9.29 g) was chromatographed over silica gel and eluted with 3:1 and 1:1 heptane-toluene. Earlier fractions contained iodoethyl benzene contaminated with self-coupled products. The 80 product was obtained from later fractions, after crystallization from a mixture of isopropanol and toluene, 1.86 g (77%), m.p. 201-203° C. Mass spec: m/z 606 (M+). Anal. Calcd. for C42H42N2S: C, 83.12; H, 6.98; N, 4.62 and S, 5.28%. Found: C, 82.95; H, 7.09; N, 4.35 and S, 5.18%. 1H NMR (CDCl3) δ ppm: 0.26 (t, 3H, 7.30 Hz), 0.37 (t, 3H, 7.30 Hz), 0.92 (t, 3H, 7.50 Hz), 1.00 (t, 3H, 7.54 Hz), 1.17 (t, 3H, 7.52 hz), 1.87 (m, 2H), 2.06 (m, 2H), 2.43 (m, 6H), 6.54 (m 2H), 6.79 (d, 1H, 7.36 Hz), 7.09 (m, 2H), 7.18 (m, 2H), 7.26 (m, 1H), 7.36 (m, 2H), 7.47 (m, 2H), 7.62 (d, 1H, 8.0 Hz), 7.89 (d, 1H, 8.0 Hz), 7.97 (dd, 1H, 1.52, 7.92 Hz), 8.05 (m, 2H). 13C NMR δ 8.28, 8.47, 13.44, 14.00, 14.27, 24.22, 24.73, 24.86, 32.64, 32.93, 56.31 (11 sp3C), 118.78, 120.84, 121.33, 121.49, 122.87, 124.03, 124.83, 125.22, 126.20, 126.64, 127.22, 127.33, 127.60, 128.23, 129.06, 130.79, 132.45, 132.93, 138.11, 143.09, 143.22, 143.40, 143.66, 145.16, 150.10, 150.42, 152.07, 154.32 and 169.06 (29 sp2C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 105℃; for 10h; Inert atmosphere; | General procedure for the preparation of products General procedure: A dried round-bottomed flask was charged with aryl iodide (0.30 mmol, 1.0 equiv), ortho-bromobenzoyl chlorides (0.36 mmol, 1.2 equiv), norbornadiene (0.60 mmol, 2.0 equiv), Pd(OAc)2 (5 mol %), triphenylphosphine (12.5 mol %), Cs2CO3 (0.675 mmol, 2.25 equiv), and DMF (4 mL). The mixture was stirred at 105 °C under nitrogen atmosphere for 10 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (5 mL) and brine (10 mL), and extracted with ethyl acetate (3 × 10 mL). The combined organic phase was washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate as eluent) to afford the target compounds |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With trifuran-2-yl-phosphane; norbornene; palladium diacetate; caesium carbonate In acetonitrile at 105℃; for 12h; Inert atmosphere; | 4.2. General procedure for the preparation of the products General procedure: A dried glassware was charged with aryl iodide 1 (1.0 equiv), acyl chlorides 2 (3.0 equiv), alkynyl carboxylative acid 3c (1.5 equiv), Pd(OAc)2 (5 mol %), tri(2-furyl)phosphine (12.5 mol %), norbornene (6.0 equiv), Cs2CO3 (5.0 equiv) in acetonitrile (4.0 mL). After stirring at 105 °C for 12 h under nitrogen, the reaction was allowed to cool to room temperature and filtered through a pad of celite with EtOAc as the eluent. The filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel using petroleum/ethyl acetate as eluent to give the target α-alkynyl aromatic ketones y, s and p. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With palladium diacetate; sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; | 20 Example 20; Preparation of (Z)-(2-(2-ethylphenyl)-1-phenyl-2-(2-(trimethylsilyl)phenyl)vinyl)trimethylsilane 0.3 mmol of sodium carbonate, 0.1 mmol of diphenylacetylene, and 0.005 mmol of palladium acetate.Bis(2-diphenylphosphinophenyl)ether 0.005 mmol, hexamethyldisilane 0.15 mmol,0.15 mmol of 2-ethyliodobenzene and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube.Nitrogen was repeatedly filled 10 times, placed in an oil bath at 100 ° C, and reacted for 24 hours;Cooled to room temperature, the reaction was diluted with ethyl acetate, washed with water three times, the organic phase dried over anhydrous Na2SO4, filtered, and concentratedPurification by thin layer chromatography to give 20.6mg of the desired product, 48% yield. |
48% | With palladium diacetate; sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(tricyclohexylphosphine)nickel(II) dichloride; 2-picoline borane complex In 1-methyl-pyrrolidin-2-one at 60℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; | ||
With bis(tricyclohexylphosphine)nickel(II) dichloride In 1-methyl-pyrrolidin-2-one at 60℃; for 18h; Inert atmosphere; | General Procedure 2: Synthesis of S-aryl isothiouronium 3,5-bis(trifluoromethyl)benzoate salts (NMP) General procedure: A microwave vial containing (Cy3P)2NiCl2 (13.8 mg, 0.020 mmol), picoline-borane (4.3 mg, 0.04 mmol), thiourea (110 mg, 1.5 mmol) and solid aryl iodide (1.0 mmol) was evacuated and back-filled with anhydrous dinitrogen three times. Liquid aryl iodides (1.0 mmol) were added subsequent to evacuation and back-filling. Anhydrous, degassed NMP (1.0 mL) was added, and the reaction was stirred at 60 °C for 18 h. After cooling to RT, the extent of conversion was determined by 1H NMR spectroscopic analysis of a 15 μL aliquot of the reaction mixture diluted with DMSO-d6. The reaction mixture was then transferred to a vial and residual reaction mixture was transferred from the microwave vial with water washes (2 × 2 mL). An aqueous solution of sodium 3,5- bis(trifluoromethyl)benzoate (1.2 M; 1.0 mL, 1.2 mmol) was added to the stirred reaction mixture. The resulting suspension was allowed to stand at 4 °C for 1 h before the solid was collected by filtration using a Büchner funnel fitted with glass filter paper. The filter cake was dried by suction for 10 minutes, then washed with ice-cold methyl tert-butyl ether (2 × 1.5 mL). Drying in vacuo afforded the S-aryl isothiouronium 3,5-bis(trifluoromethyl)benzoate salt as a free-flowing, non-hygroscopic solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With palladium diacetate; sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; | 2 Preparation of (Z)-2-(2-(1-(2-ethylphenyl)-2-phenylvinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 0.3 mmol of sodium carbonate, 0.1 mmol of diphenylacetylene, 0.005 mmol of palladium acetate, and 0.005 mmol of bis(2-diphenylphosphinophenyl)ether.0.15 mmol of pinacol borate, 0.15 mmol of 2-ethyliodobenzene and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube, and the nitrogen was repeatedly filled 10 times, and placed in an oil bath at 120 ° C. , reaction 24h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate.Wash three times with water, dry the organic phase with anhydrous Na2SO4, and filter.Concentration and purification by thin layer chromatography gave 23.7 mg of the desired product.The yield was 57%. The nuclear magnetic and high resolution mass spectra of this compound are characterized as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; 5-norbornene-2-carbonitrile; caesium carbonate In acetonitrile at 20 - 80℃; for 15h; Inert atmosphere; Sealed tube; | 1 Example 1: Preparation of Compound I-1 Add Pd2 (dba) 3 (9.2 mg, 0.01 mmol, 0.05 equivalent) to a 25.0 mL reaction flask that is dry and equipped with a magnetic stir bar,Tris (furan-2-yl) phosphine (5.2 mg, 0.022 mmol, 0.11 equivalent), cesium carbonate (163 mg, 0.5 mmol, 2.5 equivalent), under the protection of an inert gas,2-cyano-5-norbornene (48 mg, 0.4 mmol, 2.0 equivalents),1-ethyl-2-iodobenzene (92.9 mg, 0.4 mmol, 2.0 equivalents),Methyl p-toluenesulfonate (74.5 mg, 0.4 mmol, 2.0 eq), tert-butyl acrylate (25.6 mg, 0.2 mmol, 1.0 eq) and dry acetonitrile (1.0 mL). The reaction flask was stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 ° C and stirred for 15 hours. After the reaction vessel was cooled to room temperature, it was filtered through a short silica gel column, rinsed with ethyl acetate (10 mL), and concentrated under vacuum. Purified by column chromatography using petroleum ether: ethyl acetate = 50: 1 (v / v) as eluent to obtain compound I-1 (colorless oily liquid, yield 95%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With palladium diacetate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 110℃; for 18h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With palladium diacetate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 110℃; for 18h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: 1-ethyl-2-iodobenzene With norbornene; potassium acetate; palladium diacetate; potassium carbonate; triphenylphosphine In acetonitrile at 22 - 25℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: tert-Butyl chloroacetate In acetonitrile at 40℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #3: bis(pinacol)diborane In acetonitrile at 95℃; for 16h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With palladium diacetate; sodium hydrogencarbonate In chlorobenzene at 110℃; for 20h; Sealed tube; regioselective reaction; | 2 General experimental procedure for palladium-catalyzed annulation reaction General procedure: A vial equipped with a stir bar was charged with haloarene (0.10 mmol, 1 equiv), amine (0.2 mmol,2 eq), Pd(OAc)2 (0.005 mmol, 5 mol%), norbornene (0.2 mmol, 2 eq), NaHCO3 (0.2 mmol, 2 eq) and chlorobenzene (1 mL) was added and the vial was capped. The resulting mixture was heated in a sand bath at 110 °C for 20 h, cooled then filtered through a short plug of silica. Removal of the solvent gave a crude mixture which was purified by column chromatography (hexane/EtOAcgradient). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tris-(dibenzylideneacetone)dipalladium(0); bicyclo[2.2.1]hept-5-ene-2-carbonitrile; caesium carbonate; XPhos In acetonitrile at 80℃; for 15h; Schlenk technique; Inert atmosphere; | Compounds 4; General Procedure General procedure: A 25-mL oven-dried Schlenk tube equipped with a magnetic stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 0.025 equiv), XPhos (2.4 mg, 0.005 mmol, 0.025 equiv), Cs2CO3 (162.9 mg, 0.5 mmol, 2.5 equiv), and anhydrous CH3CN (1.0 mL). After stirring for about 15 min at r.t. under argon, aryl iodide 1 (0.24 mmol, 1.2 equiv), alkyl tosylate 2 (0.4 mmol, 2.0 equiv), olefin 3 (0.2 mmol, 1.0 equiv), and 5-norbornene-2-carbonitrile (4.8 mg, 0.04 mmol, 0.2 equiv) were added, then the mixture was heated to 80 °C and stirred for 15 h. After completion of the reaction (monitored by TLC), the mixture was cooled to r.t., filtered through a thin pad of Celite, eluting with EtOAc (10 mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 1,1,1,3',3',3'-hexafluoro-propanol; 3-chloro-benzenecarboperoxoic acid In water at 40 - 80℃; | 2 Example 2. Preparation of N-(4-iodo-3-ethylbenzene)-N-phenylacetamide Add 0.2mmol acetanilide, 0.3mmol 2-ethyliodobenzene, 0.3mmol m-chloroperoxybenzoic acid, 1mL hexafluoroisopropanol, and a magnet No. 5 in order. Pass the condenser tube from the bottom to the top with condensed water. The reactor was placed in a 40-80°C oil bath and heated for 2-8 hours. 15mL of water was added and extracted three times with 10mL of ethyl acetate each time. The organic phases obtained were combined and spin-dried on a rotary evaporator. The crude product was subjected to column chromatography. After separation and purification, 64.2 mg of N-(4-iodo-3-ethylbenzene)-N-acetanilide was obtained, which was a yellow solid, and the yield was 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium phenolate In dichloromethane at 50℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; | ANP-1 was synthesized according to a known procedure. 3 In a nitrogen-filled glovebox, an oven-dried 8 mL vial containing a magnetic stir bar was charged with Pd(PPh3)4 (231 mg, 0.2mmol), 1-ethyl-2-iodobenzene (232 mg, 1.0 mmol), norbornene (94 mg, 1.0 mmol), KOPh (53 mg,0.4 mmol) and 5 mL of dry DCM. The vial was capped tightly, and the mixture was vigorously stirred in a 50 oC oil bath for 12 h. After cooled to room temperature, the solid was filtered away in the glove box and the filtrate was concentrated to dryness. The residue was dissolved in drydiethyl ether (7 mL) at room temperature in the glove box and the pure complex slowly precipitated out as white solid, upon standing at room temperature (126 mg, 76% yield). The white solid wasfiltered and dried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With norborn-2-ene; trifuran-2-yl-phosphane; caesium carbonate; palladium dichloride In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | |
76% | With norborn-2-ene; trifuran-2-yl-phosphane; caesium carbonate; palladium dichloride In toluene at 80℃; for 24h; Inert atmosphere; | 2 Preparation of (E)-3-(2-ethyl-6-morpholinophenyl)allyl acetate The palladium chloride 0.01mmol, tris(2-furyl)phosphine 0.025mmol, norbornene 0.2mmol, cesium carbonate 0.25mmol, o-ethyliodobenzene 0.1mmol, morpholin-4-yl benzoate 0.18mmol, allyl acetate 0.2 mmol and 1 mL of toluene were added to a 15 mL reaction tube, filled with nitrogen repeatedly 10 times, placed in an oil bath at 80°C, and reacted for 24 hours; cooled to room temperature, filtered, concentrated, and purified by thin layer chromatography to obtain 21.9 mg of the target product. Yield Is 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 49% 2: 44% | With trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate; methyl (1S)-bicyclo<2.2.1>hept-2-eno-2-carboxylate In toluene at 105℃; for 10h; Schlenk technique; Inert atmosphere; Resolution of racemate; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; | Preparation of Substrates 4a-p and 4c-D General procedure: According to the procedure given for preparation of 4a from S1 (see above), the reaction of S3(0.798 g, 5.50 mmol) with 2-ethyliodobenzene (TCI, 1.07 g, 4.61 mmol) was carried out at roomtemperature using PdCl2(PPh3)2 (39.0 mg, 0.0556 mmol), CuI (17.0 mg, 0.0893 mmol),triethylamine (5.6 mL) and THF (10 mL). 4e (0.760 g, 2.87 mmol, 89% yield) was obtained as ayellow oil after purification by column chromatography on silica gel (eluent: hexane:Et2O:NEt3 =45:2:1) and Kugelrhor distillation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate; methyl (1S)-bicyclo<2.2.1>hept-2-eno-2-carboxylate In toluene at 105℃; for 10h; Inert atmosphere; | 3 Example 1: Preparation of chiral benzopyran 3a and chiral tertiary alcohol 1a General procedure: Under the protection of argon, add palladium acetate (1.1mg, 0.005mmol), tris(2-furyl)phosphine (4.6mg, 0.02mmol), potassium carbonate (33.2mg) to a dry reaction tube equipped with a magnetic stirrer. , 0.24mmol) and dry toluene (1.0mL), then add (1S,4R)-2-norbornene-2-carboxylic acid methyl ester (N1*) (9.1mg, 0.06mmol), 1-iodonaphthalene (2a ) (40.6 mg, 0.16 mmol) and racemic aryl tertiary alcohol (1a) (58.2 mg, 0.2 mmol). The resulting mixture was reacted at 105°C under an argon atmosphere for 24 hours. After the reaction, it was cooled to room temperature, the mixture was filtered with celite, washed with ethyl acetate, and the solvent was distilled off under reduced pressure.Column chromatography is used to separate and purify the chiral benzopyran product (S)-3a and recover the unreacted chiral tertiary alcohol (R)-1a.Chiral benzopyran product (S)-3a: colorless oily liquid, 46% yield, 94% ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With palladium diacetate; potassium carbonate; methyl (1S)-bicyclo<2.2.1>hept-2-eno-2-carboxylate In tetrahydrofuran at 110℃; for 24h; Inert atmosphere; Molecular sieve; | 3 Example 3: Preparation of Compound I-3 Under the protection of argon, add palladium acetate (2.3mg, 0.01mmol), potassium carbonate (34.6mg, 0.25mmol), potassium naphthalen-1-yltrifluoroborate (46.8mg, 0.2mmol), molecular sieves (40.0mg) and dry tetrahydrofuran (0.5mL), then add (1S, 4R)-2-norbornene-2-carboxylic acid methyl ester (7.6mg, 0.05mmol), 2-ethyl iodobenzene (23.2mg, 0.1mmol), methyl 2-bromo-3-methylbenzoate (34.4 mg, 0.15 mmol). The resulting mixture was reacted at 110°C under an argon atmosphere for 24 hours. After the reaction, it was cooled to room temperature, the mixture was filtered through Celite, and washed with ethyl acetate. Remove the solvent by distillation under reduced pressure, column chromatography was separated and purified to obtain compound I-3 (white solid, yield=53%, d.r.>20:1, e.e.=99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With pyridine; N-hydroxyphthalimide; tetrabutylammonium tetrafluoroborate; oxygen In 2,2,2-trifluoroethanol; acetonitrile at 25 - 30℃; Electrolysis; | 2.2.1 Procedure for mono-oxidation General procedure: An undivided cell was equipped with a magnet stirrer, platinum plate electrode (1.0×1.0×0.3 cm3), as the working electrode and counter electrode. Substrate (0.5 mmol),nBu4NBF4 (0.5 mmol, 164.6 mg), N-hydroxyphthalimide (NHPI, 0.1 mmol, 16.3 mg), and pyridine (1.0 mmol, 82 μL)were added to MeCN/2,2,2-trifluoroethan-1-ol (TFE) (5:1,3 mL). The electrolysis was conducted in an undivided cell equipped with O2 balloon at a constant current of 5 mA at room temperature (25-30 °C). When the reaction was completed, the solvent was removed under reduced pressure and the remaining crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate(PE/EA)=30:1-10:1) to afford the corresponding aromatic ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 8h; Inert atmosphere; | Synthesis of intermediates 1a-1e By referencing the synthesis method of 6-Phenanthridinones2, amide substrates werecoupled to 1-iodo-2-ethylbenzene or 1-iodo-2-methylbenzene to afford compound1a-1e. A flask was charged under nitrogen with Pd(OAc)2 (0.5 mmol), tri(2-furyl)phosphine (1.1 mmol), K2CO3 (20 mmol), the amides 1-5 (10 mmol), a solution ofnorbornene (12 mmol) in anhydrous DMF (20 mL), and 1-iodo-2-methylbenzene or1-iodo-2-ethylbenzene(11 mmol). The reaction mixture was heated with stirring at105 °C for 8 h and then cooled to r.t. After the addition of saturated NH4Cl (50 mL)and extraction with EtOAc (3×50 mL), the combined organic extracts were washed with brine (30 mL) and dried over Na2SO4. Removal of the solvent under reducedpressure gave the crude product, which was purified by flash chromatography onsilica gel to furnish 1a-1e as a colorless solid. (yield 75-85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With norborn-2-ene; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 12h; Inert atmosphere; | 2.1.2.5. General synthetic procedure for compounds 33-38. General procedure: A mixture ofamide substrates (1 mmol), K2CO3 (2 eq), norbornene (1.1 eq), Pd(OAc)2(0.1 eq), and TFP (0.1 eq) in 5 mL of dry DMF was placed in a two-neckround-bottom flask (rbf) under a nitrogen blanket and then refluxed at105 C for 12 h. After completion of the reaction as monitored by TLC,dilute aq NaCl solution (20 mL) was added, the organic layer wasextracted with EtOAc (20 mL), dried over anhydrous Na2SO4 andevaporated, and the crude product was purified by 100-200 columnsilica gel chromatography using PE-EtOAc as an eluent to isolate pureproducts with yields ranging from 5% to 61%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | With norborn-2-ene; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 105℃; for 12h; Inert atmosphere; | 2.1.2.5. General synthetic procedure for compounds 33-38. General procedure: A mixture ofamide substrates (1 mmol), K2CO3 (2 eq), norbornene (1.1 eq), Pd(OAc)2(0.1 eq), and TFP (0.1 eq) in 5 mL of dry DMF was placed in a two-neckround-bottom flask (rbf) under a nitrogen blanket and then refluxed at105 C for 12 h. After completion of the reaction as monitored by TLC,dilute aq NaCl solution (20 mL) was added, the organic layer wasextracted with EtOAc (20 mL), dried over anhydrous Na2SO4 andevaporated, and the crude product was purified by 100-200 columnsilica gel chromatography using PE-EtOAc as an eluent to isolate pureproducts with yields ranging from 5% to 61%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; | 30 Example 30 Under nitrogen protection, 0.03 mmol of palladium acetate, 0.075 mmol of tris-2-furylphosphine, 3 ml of dimethyl sulfoxide and 3 ml of 1,4-dioxane were sequentially added to the reaction vessel, and stirred for 10 minutes. . Then 0.9 mmol potassium carbonate, 0.6 mmol phenyl-acetyl oxime, 0.45 mmol norbornene and 0.3 mmol 1-ethyl-2-iodobenzene were added in sequence, and the reaction was stirred at 80 °C for 24 h, and the heating and stirring were stopped. , cooled to room temperature. The reaction solution was washed with saturated brine and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, distilled under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product. The eluent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1, and the yield was 68%. |
Tags: 18282-40-1 synthesis path| 18282-40-1 SDS| 18282-40-1 COA| 18282-40-1 purity| 18282-40-1 application| 18282-40-1 NMR| 18282-40-1 COA| 18282-40-1 structure
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1-Ethyl-2-iodo-3-methylbenzene
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