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Chemical Structure| 19591-17-4 Chemical Structure| 19591-17-4

Structure of 19591-17-4

Chemical Structure| 19591-17-4

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Product Details of [ 19591-17-4 ]

CAS No. :19591-17-4
Formula : C8H8INO
M.W : 261.06
SMILES Code : CC(NC1=CC=CC=C1I)=O
MDL No. :MFCD00099251
InChI Key :BCJOKHQYEDXBSF-UHFFFAOYSA-N
Pubchem ID :140559

Safety of [ 19591-17-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 19591-17-4 ]

* 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 [ 19591-17-4 ]

[ 19591-17-4 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 615-43-0 ]
  • [ 108-24-7 ]
  • [ 19591-17-4 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid; at 20℃; for 0.0833333h; One drop of concentrated H2SO4 was added to a stirred solution of 2-iodoaniline (100 mg; 0.46 mmol) in acetic anhydride (100 mL). The resulting mixture was stirred at room temperature for 5 min and then quenched with water and extracted with ethyl acetate (3 x 5 mL). The combined organic layers were washed with water, brine and dried with anhydrous sodium sulfate. The solvent was removed and the crude product was crystallized from ethanol to give the N-acetyl derivative as a crystalline solid in 85% yield, mp:102-104 C.
75% With triethylamine; In dichloromethane; at 0 - 20℃; for 19h;Inert atmosphere; 2-Iodoaniline (2.2 g, 10.1 mmol, 1.0 equiv) and triethylamine (3.1 mL, 22.2 mmol, 2.2 equiv) weredissolved in CH2Cl2 (25 mL) under argon atmosphere at rt, followed by dropwise addition of aceticanhydride (1.2 mL, 12.1 mmol, 1.2 equiv) at 0 C. The mixture stirred over night at roomtemperature to completion after 19 h, as judged by TLC. The reaction was quenched with water andextracted with CH2Cl2. The combined organic phases were washed with saturated solutions ofsodium bicarbonate and ammonium chloride, dried over anhydrous magnesium sulfate andconcentrated under vacuum. The crude product was purified by column chromatography (pentane:EtOAc 4:1) to give amide 8 (1.987 g, 7.61 mmol, 75%) as colorless crystals.
58% With triethylamine; at 20℃; for 16h;Inert atmosphere; A mixture of 2-iodoaniline (2.2 g, 10.0 mmol), Ac2O (1.2 g, 12.0 mmol) and Et3N (2.2 g, 22 mmol) in DCM was degassed with nitrogen, the mixture was stirred for 16 hours at r.t. The reaction was concentrated in vacuo. The residue was purified by column chromatography to give N-(2-iodophenyl)acetamide (1.6 g, 58% yield) as a white solid. LC/MS (ESI, m/z): [M+1]+=262.1.
With glacial acetic acid; zinc powder; at 20 - 80℃; for 3.5h; 2-Iodoanilines 21,24,25 (2. 2 g, 0.01 mole) were added separately to the mixture of aceticacid (5 mL, 0.08 mole) and acetic anhydride (1.02 g, 0.01 mole) in presence of smallamount of zinc dust and stirred at room temperature for half an hour. The reactionmixture was refluxed for 3 hours with constant stirring at 80 C. The hot reaction mixturewas poured into a beaker containing 200 mL of cold water with constant stirring andextracted with chloroform (3x50 mL). The combined organic layer was washed withdistilled water, dried over anhyd. Na2SO4 and concentrated under reduced pressure. Thecrude product was purified by chromatography on a column of silica gel andcrystallization from ethanol to afford desired products 1-3 in good yield.

  • 5
  • [ 22121-86-4 ]
  • [ 19591-17-4 ]
  • [ 116922-15-7 ]
  • 6
  • [ 39491-65-1 ]
  • [ 19591-17-4 ]
  • [ 127230-09-5 ]
  • 7
  • [ 19591-17-4 ]
  • [ 120789-51-7 ]
  • 1-[2-(tert-Butyl-dimethyl-silanyl)-3-hydroxymethyl-indol-1-yl]-ethanone [ No CAS ]
  • 8
  • [ 19591-17-4 ]
  • [ 148493-34-9 ]
  • [ 148493-40-7 ]
YieldReaction ConditionsOperation in experiment
69% With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere; A mixture of N-(2-iodophenyl)acetamide (261 mg, 1.0 mmol), <strong>[148493-34-9](2,6-dichloropyridin-3-yl)boronic acid</strong> (230 mg, 1.2 mmol), palladium acetate (11 mg, 0.05 mmol), PPh3 (26 mg, 0.1 mmol) and Et3N (303 mg, 3.0 mmol) in DMF was degassed with nitrogen, heated to 100 C. and stirred for 16 hours. The mixture was cooled to r.t, diluted with water and extracted with EA. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-(2,6-dichloropyridin-3-yl)phenyl)acetamide (180 mg, 69% yield) as a white solid. LC/MS (ESI, m/z): [M+1]+=282.1
68% With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 6h;Inert atmosphere; Step 1: Synthesis of N-[2-(2,6-dichloro-3-pyridinyl)phenyl]acetamide First, 18.94 g of 2-iodophenylacetamide, 20.73 g of <strong>[148493-34-9]2,6-dichloropyridin-3-boronic acid</strong>, 1.18 g of triphenylphosphine, 0.49 g of palladium acetate, 30 mL of triethylamine, and 290 mL of dry DMF were put into a three-neck flask equipped with a reflux pipe, and the air in the flask was replaced with nitrogen. After that, stirring was performed at 100 C. for 6 hours. Water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline and dried with magnesium sulfate, and then purified by silica gel column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 2:1 to give an objective substance as yellow-white powder in a yield of 68%. A synthesis scheme of Step 1 is shown in (a-1).
  • 9
  • [ 19591-17-4 ]
  • [ 107-19-7 ]
  • N-(2-(3-hydroxyprop-1-yn-1-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)as a white solid.
92% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: In a round-bottomed flask (50 mL) equipped with <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> [3] (0.8 g, 3.06 mmol), Pd(PPh3)2Cl2 (0.05 g, 0.08 mmol), CuI (0.03 g, 0.15 mmol) and acetonitrile (20 mL), was added 2-methyl-3-butyne-2-ol (0.33 mL, 3.37 mmol) and Et3N (1.71 mL, 12.25 mmol). The mixture was stirred at room temperature for 6-8 h. Upon completion of the reaction (TLC), the mixture was filtered, the solid residue washed with EtOAc and washings added to the filtrate. The combined solution was concentrated under reduced pressure. The oily material obtained was subjected to column chromatography (hexane/ethyl acetate 4:1) to afford the desired product 1a. Propargyl alcohols 1b-1m were prepared by using the same experimental procedure. Among these compounds, 1a and 1d are known.
  • 10
  • [ 615-43-0 ]
  • [ 75-36-5 ]
  • [ 19591-17-4 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine; In dichloromethane; at 0 - 20℃; A solution of 2-iodoaniline (333.6 mg, 1.52 mmol, 1.0 equiv) in DCM (5.0 mL) was added with Et3N (0.23 mL, 166.9 mg, 1.65 mmol, 1.1 equiv). The reaction solution was cooled at 0 C and acetyl chloride (0.28 mL, 308 mg, 3.92 mmol, 2.6 equiv) was added into the cooled solution. The resulting mixture was warmed to stir at room temperature overnight. Upon completion, thereaction was added with water and the separated aqueous phase was extracted with EtOAc (3xtimes). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30% EtOAc-hexane to yield 387.9 mg (98%) of the corresponding N-(2-iodophenyl)acetamide as a white solid.
83% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 6h; General procedure: Acyl chloride (1.5 equiv) in 5 mL of dry THF was added drop- wise to a stirred, cooled (0-5 C) solution of 2-iodoaniline ( 3 ) (1.0 equiv) and Et 3 N (1.5 equiv) in 20 mL of dry THF. The ice bath was then removed, and the mixture stirred vigorously for 6 hours at room temperature. Solid Et 3 N.HCl was then filtered off, and the fil- trate was washed with THF (3 ×5 mL). The resulting organic frac- tions were combined, and THF was removed under reduced pres- sure to afford the crude amides. Recrystallization from hexanes and drying in a vacuum produced the desired product (4a-4e) [11] .
82% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; To a solution of 2-iodoaniline (23.6 g, 108 mmol) in DCM (250 mL) was added TEA (13.1 g, 129 mmol) and cooled to 0 C. Then acetylchloride (9.30 g, 119 mmol) was added to the reaction mixture at 0 C. by dropwise and stirred at 20 C. for 2 hours. On completion, the reaction mixture was quenched by water (200 mL) and extracted with dichloromethane (3×100 mL). The extracts was washed by brine (100 mL) and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to get the crude residue. The residue was purified by column chromatography (SiO2, petroleum ether:dichloromethane:ethyl acetate=1:0:0 to 10:5:1) to give the title compound (25 g, 82% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.21 (d, J=7.6 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.48 (s, 1H) 7.35 (td, J1=1.2 Hz, J2=8.4 Hz, 1H), 6.85 (t, J=7.2 Hz, 1H), 2.25 (s, 3H); LC-MS (ESI, m/z): [M+1]+=261.7.
54% In toluene; at 20℃; for 3h; General procedure: To a solution of o-iodoaniline(2 mmol) in dry toluene (10 mL), acid chloride (2.4 mmol) was addedand the resulting mixture was stirred at room temperature for 3 h. Then, dichloromethane(20 mL) and HCl (1N, 20 mL) were added. The organic layer was separated and driedover anhydrous Na2SO4 and concentrated. The crude residuewas purified by column chromatography.
With pyridine; at 0 - 20℃; for 3h; Example 37; 2-Cyclopropyl-l-[4-(3-pyrrolidin-l-ylpropoxy)phenyl]-li-indoIe; iV~(2-Iodophenyl)acetamide; 2-Iodoaniline (1.00 g, 4.56 mmol) was dissolved in pyridine (5 mL) and cooled to 0 C. After acetyl chloride (314 μL5 5.94 mmol) was added, the reaction was stirred at 0 C for 1 hour and then at room temperature for 2 hours. The reaction was diluted with 1 N HCl and extracted with ether. The organic layer was dried (MgSO4) and EPO <DP n="38"/>concentrated to give the desired acetamide (assumed quantitative), which was used in the next reaction without further purification.
In dichloromethane; at 20℃; for 24h; General procedure: To a solution of o-haloaniline (4.63 mmol) in dry DCM (20 mL) at room temperature was dropped acyl chloride (5.09 mmol). The reaction mixture was stirred for 24 hours then poured into water, extracted with DCM, washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The product was carried on to next step without any further purification in most cases.
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 0.666667h; General procedure: The procedure consists of two steps. First, to a stirred, cooled (0-5C) solution of 2-bromoaniline (2.190g, 10mmol) and Et3N (1.113g, 1.55ml, 11mmol) in 20ml of dry THF, a solution of an appropriate acyl chloride (10mmol) in 5ml of dry THF was added dropwise within 10min. Then the ice bath was removed and the mixture was stirred vigorously for 30min at room temperature. Then, solid Et3NHCl was filtered off and washed with THF (3×5ml). The resulting organic fractions were combined and THF was removed under reduced pressure to yield crude amides. Recrystallization from hexane/CHCl3 and drying in vacuum afforded the analytically pure intermediate compounds: N-(2-bromophenyl)acylamides. In the second step, to a stirred suspension of NaH (0.132g; 5.5mmol) in 5ml of dry THF at 0C the respective amide (5mmol) dissolved in 10ml of THF was added dropwise within 10min. The reaction mixture was stirred until the solution became clear (30min, hydrogen gas evolved), and the solution of MeI (0.923g; 0.405ml; 6.5mmol) in 5ml of THF was added dropwise within 10min. The solution was warmed up to room temperature and stirred for 3-8h. Then, the reaction mixture was quenched with water (30ml). The resulting solution was extracted with ethyl acetate (3×20ml). Combined organic layers were washed with brine (1×20ml) and dried over Na2SO4. Ethyl acetate was removed under reduced pressure to give crude 1a-r. Recrystallization from hexane and drying in vacuum afforded analytically pure compounds 1a-r. In the case of (1n) and (1o), the same procedure was conducted but instead of MeI, ethyl bromide and benzyl bromide were respectively used. In the case of (1p), 2-bromopyridin-3-amine was used instead of 2 bromoaniline. In the case of (1a-Cl) and (1a-I), the same procedure was conducted but instead 2-bromoaniline, 2-chloro- and 2-iodoaniline were respectively used.

  • 12
  • [ 19591-17-4 ]
  • [ 142-29-0 ]
  • [ 126087-55-6 ]
  • 13
  • [ 19591-17-4 ]
  • [ 4187-87-5 ]
  • N-(2-(3-hydroxy-3-phenylprop-1-yn-1-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: In a round-bottomed flask (50 mL) equipped with <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> [3] (0.8 g, 3.06 mmol), Pd(PPh3)2Cl2 (0.05 g, 0.08 mmol), CuI (0.03 g, 0.15 mmol) and acetonitrile (20 mL), was added 2-methyl-3-butyne-2-ol (0.33 mL, 3.37 mmol) and Et3N (1.71 mL, 12.25 mmol). The mixture was stirred at room temperature for 6-8 h. Upon completion of the reaction (TLC), the mixture was filtered, the solid residue washed with EtOAc and washings added to the filtrate. The combined solution was concentrated under reduced pressure. The oily material obtained was subjected to column chromatography (hexane/ethyl acetate 4:1) to afford the desired product 1a. Propargyl alcohols 1b-1m were prepared by using the same experimental procedure. Among these compounds, 1a and 1d are known.
  • 14
  • [ 19591-17-4 ]
  • [ 74-88-4 ]
  • [ 90585-26-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: The procedure consists of two steps. First, to a stirred, cooled (0-5C) solution of 2-bromoaniline (2.190g, 10mmol) and Et3N (1.113g, 1.55ml, 11mmol) in 20ml of dry THF, a solution of an appropriate acyl chloride (10mmol) in 5ml of dry THF was added dropwise within 10min. Then the ice bath was removed and the mixture was stirred vigorously for 30min at room temperature. Then, solid Et3NHCl was filtered off and washed with THF (3×5ml). The resulting organic fractions were combined and THF was removed under reduced pressure to yield crude amides. Recrystallization from hexane/CHCl3 and drying in vacuum afforded the analytically pure intermediate compounds: N-(2-bromophenyl)acylamides. In the second step, to a stirred suspension of NaH (0.132g; 5.5mmol) in 5ml of dry THF at 0C the respective amide (5mmol) dissolved in 10ml of THF was added dropwise within 10min. The reaction mixture was stirred until the solution became clear (30min, hydrogen gas evolved), and the solution of MeI (0.923g; 0.405ml; 6.5mmol) in 5ml of THF was added dropwise within 10min. The solution was warmed up to room temperature and stirred for 3-8h. Then, the reaction mixture was quenched with water (30ml). The resulting solution was extracted with ethyl acetate (3×20ml). Combined organic layers were washed with brine (1×20ml) and dried over Na2SO4. Ethyl acetate was removed under reduced pressure to give crude 1a-r. Recrystallization from hexane and drying in vacuum afforded analytically pure compounds 1a-r. In the case of (1n) and (1o), the same procedure was conducted but instead of MeI, ethyl bromide and benzyl bromide were respectively used. In the case of (1p), 2-bromopyridin-3-amine was used instead of 2 bromoaniline. In the case of (1a-Cl) and (1a-I), the same procedure was conducted but instead 2-bromoaniline, 2-chloro- and 2-iodoaniline were respectively used.
  • 15
  • [ 19591-17-4 ]
  • [ 29325-49-3 ]
YieldReaction ConditionsOperation in experiment
45% With copper(I) thiophene-2-carboxylate; copper; In dimethyl sulfoxide; at 65℃; General procedure: (0013) A mixture of aryl halide (1 equiv), Cu(0) powder (10 equiv), and CuTC (2 equiv) in DMSO (0.2 mL/mmol of aryl halide) was stirred at 65-70 C for 15-72 h. Water and EtOAc were added, and the two phases were separated. The aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product which was further purified by preparative TLC (EtOAc/hexanes) to furnish the desired product.
33% With copper; In N,N-dimethyl-formamide; for 1h;Reflux; General procedure: In a 25-mL, round-bottom flask, N-(2-bromophenyl)acetamide 1 (2.0 mmol, 1.0 equiv) was dissolved in DMF (10 mL), followed by the addition of Cu(0) powder (0.38 g, 6.0 mmol, 3.0 equiv). The mixture was stirred at reflux temperature until completion. After completion, the mixture was cooled to r.t. and extracted with CH2Cl2, and the com- bined organic extracts were washed with brine solution. The organic layer was dried (anhyd MgSO4), and the solvents were removed under reduced pressure. The crude product was purified by flash chromatography (EtOAc/CH2Cl2). 2,2’-bis(acetamido)biphenyl (2a). White solid; yield: 0.12 g (43 %); mp 166.0-166.5 C; Rf = 0.15 (EtOAc/CH2Cl2 1:5). 1H NMR (400 MHz, CDCl3): δ = 8.05 (d, J = 8.0 Hz, 2 H), 7.43 (td, J = 7.7, 1.5 Hz, 2 H), 7.27-7.19 (m, 4 H), 7.03 (br s, 2 H), 1.95 (s, 6 H). 13C NMR (100 MHz, CDCl3): δ = 169.1, 135.3, 130.4, 129.2, 129.2, 125.2, 123.5, 24.0.
  • 19
  • [ 19591-17-4 ]
  • [ 71032-10-5 ]
  • exo-1-(2,3,4,4a-tetrahydro-1H-1,4-methanocarbazol-9(9aH)-yl)ethanone [ No CAS ]
  • 22
  • [ 1666-13-3 ]
  • [ 19591-17-4 ]
  • N-(2-(phenylselanyl)phenyl)acetamide [ No CAS ]
  • 23
  • [ 71460-02-1 ]
  • [ 19591-17-4 ]
  • methyl 5-[2-(acetylamino)phenyl]-2-[(tert-butoxycarbonyl)amino]-4-pentynoate [ No CAS ]
  • 26
  • [ 19591-17-4 ]
  • [ 109-89-7 ]
  • [ 106-96-7 ]
  • N-[2-(3-diethylamino-prop-1-ynyl)-phenyl]-acetamide [ No CAS ]
  • 27
  • [ 591-87-7 ]
  • [ 19591-17-4 ]
  • [ 95-20-5 ]
  • 28
  • [ 103-19-5 ]
  • [ 19591-17-4 ]
  • N-[2-(4-methylphenylthio)phenyl]acetamide [ No CAS ]
  • 29
  • [ 766-96-1 ]
  • [ 19591-17-4 ]
  • N-(2-((4-bromophenyl)ethynyl)phenyl)acetamide [ No CAS ]
  • 30
  • [ 19591-17-4 ]
  • [ 1066-54-2 ]
  • [ 110598-59-9 ]
YieldReaction ConditionsOperation in experiment
77% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; General procedure: Toa solution of 2-iodoarenes 1 (1 mmol)in dry THF/Et3N (2:1, 10 mL) were added Pd(PPh3)2Cl2(0.025 mmol) and CuI (0.05 mmol) under argon atmosphere. Trimethylsilyl acetylene2 (1.3 mmol) was then added dropwiseand the resulting mixture was stirred at room temperature for 4 h (TLC). Thereaction mixture was concentrated under reduced pressure and the residue waspurified by silica gel (100-200 mesh) column chromatography using diethyl etherin petroleum ether (4-10%) to afford the pure2-((trimethylsilyl)ethynyl)arenes3 in good to excellent yields (Table1).
65% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere; A mixture of substituted <strong>[19591-17-4]2-iodoacetanilide</strong> 1-3 (500 mg, 1.92 mmol),bis(triphenylphosphine)palladium(II)chloride (47.30 mg, 1.92 mmol), copper (II) iodide(29.3 mg,1.92 mmol), and trimethylsilylacetylene (387 mg, 1.92 mmol) was stirred inDMF (5-7 mL) under nitrogen atmosphere. Then triethylamine (780 mg, 1.92 mmol) wasadded drop wise to this mixture and stirring continued at room temperature for 24-48 h.The mixture was evaporated to dryness under reduced pressure. The residue extracted with chloroform (3×50 mL), the combined chloroform extracts washed with distilledwater (3×50 mL), dried over anhydrous Na2SO4, filtered and concentrated under reducedpressure. The crude product was purified by column chromatography on silica gel usingpet ether/chloroform (3:1) as eluant to afford the desired compounds 5-7 in good yield.
  • 31
  • 1-(tert-butyldimethylsiloxy)-2-(tributylstannyl)-2,3-butadiene [ No CAS ]
  • [ 19591-17-4 ]
  • 1-[3-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-2-methyl-indol-1-yl]-ethanone [ No CAS ]
  • 32
  • 1-(tert-butyldimethylsiloxy)-2-(tributylstannyl)-2,3-butadiene [ No CAS ]
  • [ 19591-17-4 ]
  • <i>N</i>-{2-[1-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-propa-1,2-dienyl]-phenyl}-acetamide [ No CAS ]
  • 33
  • [ 871-84-1 ]
  • [ 19591-17-4 ]
  • 1-(1,7-octadiynyl)-2-acetamidobenzene [ No CAS ]
  • 34
  • [ 629-05-0 ]
  • [ 19591-17-4 ]
  • N-[2-(1-octynyl)phenyl]acetamide [ No CAS ]
  • 35
  • [ 19591-17-4 ]
  • N-(2-iodylphenyl)acetamide [ No CAS ]
  • 37
  • [ 19591-17-4 ]
  • <i>N</i>-(2-iodo-6-oxo-cyclohexa-2,4-dienylidene)-acetamide [ No CAS ]
  • 38
  • 1-(2-iodophenyl)ethanone oxime [ No CAS ]
  • [ 19591-17-4 ]
  • 39
  • [ 19591-17-4 ]
  • [ 13139-86-1 ]
  • [ 1217-87-4 ]
  • 40
  • [ 19591-17-4 ]
  • [ 292638-85-8 ]
  • [ 177411-39-1 ]
  • 41
  • [ 19591-17-4 ]
  • [ 141-43-5 ]
  • [ 4946-08-1 ]
  • 42
  • [ 19591-17-4 ]
  • [ 120-75-2 ]
YieldReaction ConditionsOperation in experiment
84% General procedure: To an oven-dried Schlenk tube were added Na2S•9H2O (or K2S, 3.0mmol), o-haloanilide (1.0 mmol), and MCM-41-NHC-CuI (228 mg, 0.1 mmol). The tube was sealed and then evacuated and backfilled withargon, and DMF (2 mL) was injected with a syringe. The mixture washeated to 80 C with stirring for 12 h (140 C and 24 h for o-bromoanilide).Upon cooling to ambient temperature, the mixture was centrifugatedto separate the copper catalyst. The catalyst recovered waswashed with deionized water (3 × 2 mL) and acetone (3 × 2 mL) anddried in vacuo at 80 C for 1 h, and used in the next run. Then conc. HCl(0.8 mL) was added into the resultant solution. After stirring for 10 h atambient temperature, 10 mL saturated aq. NaHCO3 was added into thesolution and the resulting mixture was then extracted with EtOAc forthree times. After being washed with water and brine, the organic layerwas dried over anhydrous MgSO4 and concentrated under the reducedpressure. The residue was then purified via column chromatography onsilica gel (hexane/ethyl acetate) to furnish the expected product 2.
  • 43
  • [ 6746-94-7 ]
  • [ 19591-17-4 ]
  • C13H13NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N,N',N'-tetramethylguanidine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In 1,4-dioxane; at 80℃; 2~Cyclopropyl-12/~mdole; To a solution of iV-(2-iodophenyl)acetamide (100 mg, 0.38 mmol) in dioxane (750 mL) and 1,1,3,3-tetramethylguanidine (750 mL) was added cyclopropylacetylene (41 mL, 0.49 mmol), bis(triphenylphosphine)palladium(II) chloride (35 mg, 0.05 mmol), and copper(I) iodide (10 mg, 0.05 mmol). The reaction was stirred overnight at 80 0C. The solution was cooled and partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the uncyclized Sonagashira coupling product. Dioxane (750 mL) and 1,1,3,3-tetramethylguanidine (750 mL) were added and the reaction was stirred overnight at 90 C. The solution was again partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the desired indole, which was used without further purification.
  • 46
  • [ 24424-99-5 ]
  • [ 19591-17-4 ]
  • [ 1088145-67-8 ]
  • 47
  • [ 19591-17-4 ]
  • [ 536-74-3 ]
  • [ 78388-91-7 ]
YieldReaction ConditionsOperation in experiment
82% With potassium phosphate; diethylzinc; N,N`-dimethylethylenediamine; In acetonitrile; at 125℃; for 12h;Sealed tube; Inert atmosphere; General procedure: A dry sealed tube was charged with 1.1 mmol (271 mg) of 2-iodophenol and 2 equiv. of K3PO4 (424 mg). To the above mixture was added 1 mmol of phenylacetylene (102 mg, 0.109 ml), 5 mol % of Et2Zn (0.05 ml), 10 mol % of DMEDA (0.01 ml) and 3 ml of acetonitrile under nitrogen. The sealed tube was heated in an oil bath which was preheated to 125 C and the reaction mixture was stirred under the same conditions for 12 hours. The reaction mixture was then cooled and extracted with ethyl acetate (3 x 15 ml) and the ethyl acetate layer was washed with distilled water. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure in a rotary evaporator. The crude residue was purified by column chromatography using hexane as the eluent to get 180 mg (93 %) of the product as a colourless solid. All other benzofuran derivatives were synthesized by similar procedure.
  • 48
  • [ 931-49-7 ]
  • [ 19591-17-4 ]
  • [ 1098336-36-7 ]
YieldReaction ConditionsOperation in experiment
> 99% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)as a white solid.
  • 49
  • [ 19591-17-4 ]
  • [ 107-13-1 ]
  • [ 72592-64-4 ]
  • 50
  • [ 1189795-79-6 ]
  • [ 19591-17-4 ]
  • [ 1189794-10-2 ]
YieldReaction ConditionsOperation in experiment
31% With sodium carbonate;[1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride; In N,N-dimethyl-formamide; at 100℃; for 24h;Inert atmosphere; b) [4-ethoxy-4-(3-methoxymethyl-1H-indol-2-yl)-1-phenyl-cyclohexyl]-dimethylamine N-(2-iodo-phenyl)-acetamide (522 mg, 2.0 mmol), the title compound of the previous step (631 mg, 2.0 mmol) and sodium carbonate (1.06 g, 10.0 mmol) were dissolved in abs. DMF (10 mL) in argon. The catalyst (PEPPSI, 272 mg, 0.4 mmol) was then added and the solution stirred for 24 h at 100 C. For work up the black reaction solution was concentrated in a vacuum until dry, the residue dissolved in CHCl3 and washed with water. The organic phase was dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with CHCl3/MeOH (50:1). Yield: 249 mg (31%) 1H-NMR (DMSO-d6): 1.11 (3H, t); 1.61 (2H, m); 1.99 (8H, m); 2.19 (2H, m); 2.48 (2H, m); 3.12 (5H, m); 4.53 (2H, s); 6.99 (2H, m); 7.27 (2H, d); 7.47 (5H, m); 10.61 (H, s).
  • 51
  • [ 19591-17-4 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • [ 1239-56-1 ]
  • 52
  • [ 19591-17-4 ]
  • diethyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate [ No CAS ]
  • C19H23N3O5 [ No CAS ]
  • 53
  • [ 52670-38-9 ]
  • [ 19591-17-4 ]
  • [ 1301267-77-5 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; General procedure: Under the protection of nitrogen, a THF solution (20 mL) containing Et3N (15 mmol) and o-ethynylaniline (6 mmol) was added to a flask containing amide (5 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.1 mmol) and CuI (0.05 mmol). The mixture was stirred overnight at room temperature (monitored by TLC). Then the solvent was removed under vacuum. The obtained residue was treated with a mixture of chloroform (30 mL) and water (30 mL). The separated organic layer was washed with brine (15 mL), dried with anhydrous MgSO4. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (EtOAc-PE, 1:2) to give N-[2-[(2-Aminophenyl)ethynyl]phenyl]amide.
  • 54
  • [ 19591-17-4 ]
  • [ 75-20-7 ]
  • [ 1338725-50-0 ]
YieldReaction ConditionsOperation in experiment
94% With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: A 100 mL round bottom flask with a magnetic stir bar was charged with copper iodide (0.1 equiv), palladium acetate (0.05 equiv), and triphenylphosphine (0.1 equiv) in acetonitrile. The solution was degassed with nitrogen for 20 min. Then, triethylamine (3 equiv), aryl iodides (1 equiv), and calcium carbide (3 equiv) were added. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The reaction mixture was then filtrated through a short plug of silica gel and washed with hexane. The filtrate was evaporated under vacuum to give the desired compound.
 

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