Home Cart 0 Sign in  
X

[ CAS No. 2296-23-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 2296-23-3
Chemical Structure| 2296-23-3
Chemical Structure| 2296-23-3
Structure of 2296-23-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 2296-23-3 ]

Related Doc. of [ 2296-23-3 ]

Alternatived Products of [ 2296-23-3 ]

Product Details of [ 2296-23-3 ]

CAS No. :2296-23-3 MDL No. :MFCD11054826
Formula : C7H4INO Boiling Point : -
Linear Structure Formula :- InChI Key :XAONDNGLTPLRKO-UHFFFAOYSA-N
M.W : 245.02 Pubchem ID :10955815
Synonyms :

Calculated chemistry of [ 2296-23-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.9
TPSA : 44.02 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 : Yes
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.231 mg/ml ; 0.000943 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.795 mg/ml ; 0.00325 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.334 mg/ml ; 0.00136 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 2296-23-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2296-23-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2296-23-3 ]

[ 2296-23-3 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 767-00-0 ]
  • [ 2296-23-3 ]
  • [ 1689-83-4 ]
  • 2
  • [ 767-00-0 ]
  • [ 2296-23-3 ]
YieldReaction ConditionsOperation in experiment
82% With ammonium hydroxide; iodine; potassium iodide; In water; at 20℃; for 16h;Inert atmosphere; To a solution of 4-hydroxy-benzonitrile (5 g, CAS: 767-00-0) in NH4OH (225 mL) was added a solution of KI (34.14 g, CAS: 7681-11-0) and ?2(10.65 g, CAS: 7553-56-2) in H20 (50 mL). The reaction mixture was stirred at rt for 16 hours. The reaction mixture was filtered andthe filtrate was evaporated. The residue was dissolved in DCM (250 mL) and was washed with H20 (2x150 mL), saturated aqueous Na5203 solution (100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2504, filtered and concentrated under reduced pressure to give the title compound (8.44 g, 82%) that was used in the next step without further purification. LC-MS: (ESI): mlz = 244.0 [M-H]
80% With ammonium hydroxide; iodine; potassium iodide; In water; for 6h; To a solution of A- hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of I2 (1.06 g; 4.18 mmol) and Kl (3.41 g; 20.54 mmol) in H2O (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H2O (3 ml). The precipitate formed was filtered off, washed with cold H2O (3 x 2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1H-NMR (CDCI3) 7.96 (d, 1 H, 1 .9 Hz); 7. 53 (dd, 1 H, J = 1 .9 Hz, 8.5 Hz); 7.03 (d, 1 H, J = 8.5 Hz); 6.03 (s, 1 H);
80% With ammonia; iodine; potassium iodide; In water; for 6h; To a solution of 4- hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of I2 (1.06 g; 4.18 mmol) and Kl (3.41 g; 20.54 mmol) in H2O (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H2O (3 ml). The precipitate formed was filtered off, washed with cold H2O (3 x 2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1 H-NMR (CDCI3 ) 6.03 (s, 1 H); 7.03 (d, 1 H, J = 8.5 Hz); 7. 53 (dd, 1 H, J = 1 .9 Hz, 8.5 Hz); 7.96 (d, 1 H, 1 .9 Hz).
80% With ammonium hydroxide; iodine; potassium iodide; In water; for 6h; To a solution of 4- hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of l2 (1 .06 g; 4.18 mmol) and Kl (3.41 g; 20.54 mmol) in H20 (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H20 (3 ml). The precipitate formed was filtered off, washed with cold H20 (3 x 2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1 H-NMR (CDCI3) 7.96 (d, 1 H, 1 .9 Hz) ; 7. 53 (dd, 1 H, J = 1 .9 Hz, 8.5 Hz) ; 7.03 (d, 1 H, J = 8.5 Hz); 6.03 (s, 1 H) ;
With ammonia; iodine; In methanol; water; at 20℃; for 2h; A. 3-Iodo-4-hydroxybenzonitrile 11.9 g (0.1 mol) of 4-hydroxybenzonitrile are dissolved in 250 ml of methanol and 250 ml of 20% aqueous ammonia are added. A solution of 31.75 g of iodine in 250 ml of methanol is then added dropwise, with care, due to the explosive nature of the reaction. After addition, the mixture is stirred for 2 hours at ambient temperature. The methanol is evaporated off, dilution is carried out in water and acidification with a hydrochloric acid solution is performed until pH=2 to 3 is obtained. Extraction with ethyl acetate and washing with water, a sodium thiosulfate solution and a saturated sodium chloride solution are subsequently carried out. In this way, 24.73 g of desired compound are obtained. M.p.: 144-146 C. The compound below was prepared using the same process as above:

  • 3
  • [ 2296-23-3 ]
  • [ 74-88-4 ]
  • [ 82504-06-1 ]
YieldReaction ConditionsOperation in experiment
67% Example 87A 4-hydroxy-3-iodobenzonitrile In a 2000 mL round-bottom flask containing 10.0 g (84 mmol) of 4-cyanophenol, 450 mL conc. animonium hydroxide was added and contents were allowed to stir at 25 C. for 15 min. Next, a solution of 67.9 g (409 mmol) potassium iodide and 21.3 g (84 mmol) iodine chips, dissolved in 100 mL water, was quickly added. The reaction mixture was allowed to stir at 25 C. for 18 h at which time contents were filtered. The filtrate was concentrated under reduced pressure and redissolved in 500 mL dichloromethane. The organic layer was then washed twice with 250 mL water, dried, and concentrated under reduced pressure to provide the title compound as a light yellow solid (14.3 g, 67% yield). 1H-NMR (300 MHz, CDCl3) delta 7.03 (d, 1H), 7.66 (dd, 1H), 7.98 (s, 1H); MS DCI m/e, 263 (M+NH4)+.
  • 7
  • [ 2296-23-3 ]
  • [ 360791-76-0 ]
  • [ 360791-77-1 ]
  • 8
  • [ 2296-23-3 ]
  • [ 536-74-3 ]
  • [ 79008-77-8 ]
  • 9
  • [ 2296-23-3 ]
  • [ 10365-98-7 ]
  • [ 450842-38-3 ]
  • 10
  • [ 2296-23-3 ]
  • [ 90555-66-1 ]
  • [ 565203-86-3 ]
  • 11
  • [ 2296-23-3 ]
  • [ 82203-84-7 ]
  • 2-(4-chloro-phenyl)-3-trifluoromethyl-benzofuran-5-carbonitrile [ No CAS ]
  • 12
  • [ 2296-23-3 ]
  • [ 460747-73-3 ]
  • [ 460747-72-2 ]
  • 13
  • [ 2296-23-3 ]
  • [ 98-60-2 ]
  • 4-cyano-2-iodophenyl 4-chlorobenzenesulfonate [ No CAS ]
  • 14
  • [ 2296-23-3 ]
  • [ 100-52-7 ]
  • 4-hydroxy-3-(hydroxy-phenyl-methyl)-benzonitrile [ No CAS ]
  • 15
  • [ 2296-23-3 ]
  • [ 927-74-2 ]
  • [ 919088-04-3 ]
  • 16
  • [ 5390-04-5 ]
  • [ 2296-23-3 ]
  • 5-cyano-2-(3-hydroxyprop-1-yl)benzofuran [ No CAS ]
  • 17
  • [ 960160-63-8 ]
  • [ 2296-23-3 ]
  • [ 50638-34-1 ]
  • 18
  • [ 2296-23-3 ]
  • [ 628-16-0 ]
  • [ 50638-34-1 ]
  • 19
  • [ 2396-65-8 ]
  • [ 2296-23-3 ]
  • [ 854895-17-3 ]
  • 20
  • [ 1720-38-3 ]
  • [ 2296-23-3 ]
  • [ 84223-98-3 ]
  • 21
  • [ 4117-15-1 ]
  • [ 2296-23-3 ]
  • 1,7-bis(5-cyanobenzofuran-2-yl)heptane [ No CAS ]
  • 22
  • [ 20521-44-2 ]
  • [ 2296-23-3 ]
  • 1,8-bis(5-cyanobenzofuran-2-yl)octane [ No CAS ]
  • 23
  • [ 38628-39-6 ]
  • [ 2296-23-3 ]
  • 1,9-bis(5-cyanobenzofuran-2-yl)nonane [ No CAS ]
  • 24
  • [ 38628-40-9 ]
  • [ 2296-23-3 ]
  • 1,10-bis(5-cyanobenzofuran-2-yl)decane [ No CAS ]
  • 25
  • [ 4634-67-7 ]
  • [ 2296-23-3 ]
  • 1,11-bis(5-cyanobenzofuran-2-yl)undecane [ No CAS ]
  • 29
  • [ 2296-23-3 ]
  • 2-{2-[2-(4-methyl-piperazin-1-yl)-ethyl]-benzofuran-5-yl}-1<i>H</i>-benzoimidazole [ No CAS ]
  • 30
  • [ 2296-23-3 ]
  • 5-chloro-2-{2-[2-(4-methyl-piperazin-1-yl)-ethyl]-benzofuran-5-yl}-1<i>H</i>-benzoimidazole [ No CAS ]
  • 31
  • [ 2296-23-3 ]
  • 5-methyl-2-{2-[2-(4-methyl-piperazin-1-yl)-ethyl]-benzofuran-5-yl}-1<i>H</i>-benzoimidazole [ No CAS ]
  • 32
  • [ 2296-23-3 ]
  • 5-chloro-6-fluoro-2-{2-[2-(4-methyl-piperazin-1-yl)-ethyl]-benzofuran-5-yl}-1<i>H</i>-benzoimidazole [ No CAS ]
  • 33
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-pyrimidin-5-yl-amine [ No CAS ]
  • 34
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-pyrazin-2-yl-amine [ No CAS ]
  • 35
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-pyrimidin-2-yl-amine [ No CAS ]
  • 36
  • [ 2296-23-3 ]
  • (6-Chloro-pyridazin-3-yl)-{2-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amine [ No CAS ]
  • 37
  • [ 2296-23-3 ]
  • (5-Bromo-pyrimidin-2-yl)-{2-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amine [ No CAS ]
  • 38
  • [ 2296-23-3 ]
  • 3-({2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amino)-benzonitrile [ No CAS ]
  • 39
  • [ 2296-23-3 ]
  • (5-Ethyl-pyrimidin-2-yl)-{2-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amine [ No CAS ]
  • 40
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-(2-nitro-phenyl)-amine [ No CAS ]
  • 41
  • [ 2296-23-3 ]
  • 6-({2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amino)-nicotinonitrile [ No CAS ]
  • 42
  • [ 2296-23-3 ]
  • 3-({2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amino)-pyrazine-2-carbonitrile [ No CAS ]
  • 43
  • [ 2296-23-3 ]
  • 2-({2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amino)-nicotinonitrile [ No CAS ]
  • 44
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-(3-nitro-pyridin-2-yl)-amine [ No CAS ]
  • 45
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-(4-nitro-phenyl)-amine [ No CAS ]
  • 46
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-(5-nitro-thiazol-2-yl)-amine [ No CAS ]
  • 47
  • [ 2296-23-3 ]
  • {2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-(5-nitro-pyridin-2-yl)-amine [ No CAS ]
  • 48
  • [ 2296-23-3 ]
  • 4-({2-[2-((R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amino)-pyridine-2,6-dicarbonitrile [ No CAS ]
  • 49
  • [ 2296-23-3 ]
  • (3,5-Dinitro-pyridin-2-yl)-{2-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amine [ No CAS ]
  • 50
  • [ 2296-23-3 ]
  • 2,2,2-Trifluoro-1-[4-({2-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-ylmethyl}-amino)-phenyl]-ethanone [ No CAS ]
  • 51
  • [ 2296-23-3 ]
  • 11-oxa-tricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-4-carbonitrile [ No CAS ]
  • 58
  • [ 2296-23-3 ]
  • 6-{3-[3-(4-cyano-benzyl)-3<i>H</i>-imidazol-4-yl]-3-hydroxy-prop-1-ynyl}-3'-methoxy-biphenyl-3-carbonitrile [ No CAS ]
  • 59
  • [ 2296-23-3 ]
  • 6-{3-[3-(4-cyano-benzyl)-3<i>H</i>-imidazol-4-yl]-3-hydroxy-prop-1-ynyl}-3'-ethoxy-biphenyl-3-carbonitrile [ No CAS ]
  • 60
  • [ 2296-23-3 ]
  • 2-(2-hydroxy-biphenyl-3-yl)-benzofuran-5-carboxamidine [ No CAS ]
  • 61
  • [ 2296-23-3 ]
  • [ 1026799-01-8 ]
  • 62
  • [ 2296-23-3 ]
  • <i>N</i>-hydroxy-2-[2-(2-methoxy-ethoxymethoxy)-biphenyl-3-yl]-benzofuran-5-carboxamidine [ No CAS ]
  • 63
  • [ 2296-23-3 ]
  • C27H26N2O6 [ No CAS ]
  • 64
  • [ 2296-23-3 ]
  • [ 82504-07-2 ]
  • 65
  • [ 2296-23-3 ]
  • [ 82504-09-4 ]
  • 66
  • [ 2296-23-3 ]
  • [ 82504-08-3 ]
  • 67
  • [ 2296-23-3 ]
  • Acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester [ No CAS ]
  • 68
  • [ 2296-23-3 ]
  • [ 82504-10-7 ]
  • 69
  • [ 2296-23-3 ]
  • [ 76193-27-6 ]
  • 70
  • [ 624-24-8 ]
  • [ 2296-23-3 ]
  • [ 401840-73-1 ]
YieldReaction ConditionsOperation in experiment
59% With N,N,N1,N1-tetramethylguanidine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In DMF (N,N-dimethyl-formamide); at 20℃; for 20h; B. Methyl 3-(5-cyano-1-benzofuran-2-yl)propanoate 19.38 g (79 mmol) of compound obtained in the preceding step, 9.81 g (1.1 equivalents) of methyl 4-pentanoate, 0.750 g (0.05 equivalent) of copper iodide, 2.77 g of dichlorobis(triphenylphosphine)-palladium and 100 ml (10 equivalents) of tetramethylguanidine are introduced into 125 ml of N,N-dimethylformamide. The mixture is stirred at ambient temperature for 20 hours, diluted with 1000 ml of water and extracted with 600 ml of ethyl acetate. Washing is carried out with water, dilute hydrochloric acid, water and a saturated sodium chloride solution. Purification is subsequently carried out by chromatography on silica (eluent: 100/1 dichloromethane/ethyl acetate). In this way, 9.93 g of desired compound are obtained. Yield: 59% M.p.: 91-92 C. The following compound was obtained by following the same process as above:
  • 71
  • [ 889884-74-6 ]
  • [ 2296-23-3 ]
  • [ 889884-75-7 ]
YieldReaction ConditionsOperation in experiment
35% A mixture of <strong>[2296-23-3]4-cyano-2-iodophenol</strong> (1.23 g, 5 mmol), silylated alkyne (from step i) (2.18 g, 5 mmol), LiCl (0.21 g, 5 mmol) and Na2CO3 (2.38 g, 22.5 mmol) in 20 ml DMF was degassed by bubbling nitrogen through the solution for 2 h. Pd(OAc)2 (50 mg, 0.20 mmol) was added and the reaction mixture was stirred for 7 hours at 100 C. H2O and hexane were added and the mixture was filtered over hyflo. After separation of the hexane layer, the aqueous layer was extracted with hexane (1×). The combined hexane layers were washed with H2O (1×) and brine 1×). The hexane fraction was partially evaporated under reduced pressure and 8 g of silicagel was added and stirring was continued for 15 minutes. The silica is filtered off and the filtrate is concentrated under reduced pressure. The residue was chromatographed (SiO2) using Et2O/petroleum ether 1/9 as the eluent to give 0.93 g (35%) of the benzfurane derivative as a light yellow oil.
  • 72
  • [ 60032-63-5 ]
  • [ 6192-52-5 ]
  • [ 7487-88-9 ]
  • [ 2296-23-3 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; In 5,5-dimethyl-1,3-cyclohexadiene; REFERENCE EXAMPLE 12 4-Hydroxy-3-Iodo-Benzonitrile To a solution of 4-hydroxy-3-iodo-benzaldehyde (7.9 g, 31.8 mmol) (prepared by the method of Barnes at al.; J. Chem. Soc., 1950, 2824) in xylene (120 mL) was added hydroxylamine hydrochloride (2.34 g, 33.4 mmol), magnesium sulphate (12.7 g) and p-toluene sulphonic acid monohydrate (1.27 g, 6.4 mmol). The resulting mixture was heated to reflux and stirred at this temperature for 90 min. The reaction mixture was then allowed to cool to room temperature and filtered. The solid was washed with ethyl acetate then the combined filtrates concentrated. The residue was purified by flash chromatography (eluding with 30% ethyl acetate in hexanes) to give 6.57 g of the title compound. 1H NMR (CDCl3) d 6.1 (bs, 1H), 7.05 (d, J=8 Hz, 1H), 7.55 (dd, J=8, 1 Hz, 1H), 7.99 (d, J=1 Hz, 1H).
  • 73
  • [ 17642-18-1 ]
  • [ 2296-23-3 ]
  • methyl 4-[4-cyano-2-iodo-phenoxy]-but-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; NaH; In tetrahydrofuran; mineral oil; Methyl 4-[4-Cyano-2-Iodo-Phenoxy]-But-2-enoate To a cooled (0 C.) suspension of NaH (1.5 g of 60% suspension in mineral oil, 38 mmol) in THF (80 mL) was added a solution comprised of <strong>[2296-23-3]4-hydroxy-3-iodo-benzonitrile</strong> (8.4 g, 34 mmol) (reference example 12), methyl bromo-crotonate (6.65 mL tech. grade, approx. 51 mmol) and DMPU (10 mL) in THF (20 mL). On complete addition, the cold bath was removed and replaced with an oil bath. The reaction mixture was heated to 55 C. and stirred at this temperature for 4.5 hr, cooled to room temperature and acidified with 2M aqueous HCl. The mixture was then diluted with ethyl acetate, washed sequentially with water and brine, dried over MgSO4 and concentrated. The residue was triturated with hexane several times, leaving 8.6 g of the title compound as a solid. 1H NMR (CDCl3) d 3.78 (s, 3H), 4.80 (dd, J=4, 1 Hz, 1H), 6.35 (dt, J=16, 1 Hz, 1H), 6.79 (d, J=8 Hz, 1H), 7.05 (dt, J=16, 4 Hz, 1H), 7.60 (dd, J=8, 1 Hz, 1H), 8.06 (d, J=1 Hz, 1H). MS (EI) m/z 343 (M)+.
  • 74
  • [ 60032-63-5 ]
  • [ 2296-23-3 ]
YieldReaction ConditionsOperation in experiment
58% With hydroxylamine hydrochloride; sodium acetate; In formic acid; at 105℃; for 3h; INTERMEDIATE 404-Hvdroxy-3-iodobenzonitrileTo a stirred solution of Intermediate 39 (5.2 g, 20.97 mmol) in formic acid (60 mL) was added sodium acetate (2.1 g, 25.16 mmol), followed by hydroxylamine hydrochloride (8.7 g, 125.8 mmol). The reaction mixture was stirred at 1050C for 3 h, then cooled to r.t. and poured onto water. The solid formed was filtered to give the title compound (3.0 g, 58%) as a white solid that was used without further purification. LCMS (ES+) 246.1 (M+H)+, RT 1.64 minutes (Method 11).
With hydroxylamine hydrochloride; sodium acetate; In formic acid; at 105℃; for 3h; To a stirred solution of Intermediate 39 (5.2 g, 20.97 mmol) in formic acid (60 mL) was added sodium acetate (2.1 g, 25.16 mmol), followed by hydroxylamine hydrochloride (8.7 g, 125.8 mmol). The reaction mixture was stirred at 105 C. for 3 h, then cooled to r.t. and poured onto water. The solid formed was filtered to give the title compound (3.0 g, 58%) as a white solid that was used without further purification. LCMS (ES+) 246.1 (M+H)+, RT 1.64 minutes (Method 11).
  • 75
  • [ 914105-99-0 ]
  • [ 2296-23-3 ]
  • [ 1072911-79-5 ]
  • 76
  • [ 204919-70-0 ]
  • [ 2296-23-3 ]
  • [ 1072911-80-8 ]
  • 77
  • [ 2296-23-3 ]
  • [ 3032-92-6 ]
  • [ 28718-79-8 ]
  • 78
  • [ 2296-23-3 ]
  • [ 171290-53-2 ]
  • [ 1017259-38-9 ]
  • 79
  • [ 2296-23-3 ]
  • [ 1066-54-2 ]
  • C12H13NOSi [ No CAS ]
  • 80
  • [ 768-70-7 ]
  • [ 2296-23-3 ]
  • [ 77084-12-9 ]
  • 81
  • [ 2296-23-3 ]
  • [ 768-60-5 ]
  • [ 1186301-59-6 ]
  • 82
  • [ 764-93-2 ]
  • [ 2296-23-3 ]
  • [ 1218818-18-8 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine;copper(l) iodide; palladium diacetate; CyJohnPhos; In acetonitrile; at 60℃; for 18h; To a stirred solution of <strong>[2296-23-3]4-hydroxy-3-iodobenzonitrile</strong> (LXXX) (4.55 g, 18.57 mmol), 1-decyne (LXXXI) (2.57 g, 18.57 mmol), (2-biphenyl)dicyclohexylphosphine (0.325 g, 0.928 mmol), (or using same moles of triphenylphosphine) and triethylamine (5.64 g, 55.71 mmol) in acetonitrile (100 mL) was added palladium(II) acetate (0.208 g, 0.928 mmol) and copper(I) iodide (0.354 g, 1.86 mmol). The reaction mixture was heated to 60 C. After 18 hours, the reaction mixture was allowed to cool to room temperature and was concentrated. The residue was dissolved in ethyl acetate and washed with IN hydrochloric acid, 6N ammonium hydroxide, and brine. The organic phase was dried (magnesium sulfate), filtered, and concentrated to provide 5.29 g of a brown oil. Flash chromatography using an Isco Combiflash unit (90 g SiO2 column, 10-20% ethyl acetate/hexanes) afforded 2.62 g (55% yield) of 2- octylbenzofuran-5-carbonitrile (LXXXII) as a yellow solid: 1H NMR (CDCl3) delta 7.80 (s, 1H), 7.52-7.43 (m, 2H), 6.43 (s, 1H), 2.78 (t, J= 7.6 Hz, 2H), 1.80-1.69 (m, 2H), 1.44-1.20 (m, 10H), 0.88 (t, 7= 6.9 Hz, 3H) ppm.
  • 83
  • [ 2296-23-3 ]
  • [ 107-19-7 ]
  • [ 84102-78-3 ]
YieldReaction ConditionsOperation in experiment
67% With pyridine; copper(I) oxide; for 0.75h;Inert atmosphere of N2; Reflux; Propargyl alcohol (0.24 ml; 5.2 mmol) was added drop wise during 30 min to a refluxed suspension of the product of Step A (0.48 g; 1.96 mmol) and Cu2O (0.28 g; 1 .96 mmol) in anhydrous pyridine ( 4 ml) with stirring under N2. After additional reflux for 15 min, the mixture was cooled to room temperature, diluted to 20 ml with ethyl acetate (EtOAc) and insoluble material was removed by filtration. The filtrate was evaporated to dryness under reduced pressure and the residue was diluted to 20 ml with EtOAc, washed with diluted HCI (10 ml). The insoluble material formed was filtered off and the organic phase was washed with H2O (5 ml), brine, dried over anhydrous MgSO4, filtered and the filtrate evaporated to dryness. The residue was purified by flash column chromatography (FCC) (SiO2, CH2CI2 and EtOAc, 9 : 1 ) to give the title compound (0.23 g; 67%) as a colourless solid. 1H- NMR (CDCI3) 7.86 (m, 1 H); 7.49 - 7.55 (m, 2H); 6.72 (d, 1 H, J = 3 Hz); 4.8 (d, 2H, J = 3 Hz); 2.18 (broad s, 1 H);
67% With pyridine; copper(I) oxide; for 0.75h;Inert atmosphere; Reflux; Propargyl alcohol (0.24 ml; 5.2 mmol) was added drop wise during 30 min to a refluxed suspension of the product of Step A (0.48 g; 1 .96 mmol) and Cu20 (0.28 g; 1 .96 mmol) in anhydrous pyridine ( 4 ml) with stirring under N2. After additional reflux for 15 min, the mixture was cooled to room temperature, diluted to 20 ml with ethyl acetate (EtOAc) and insoluble material was removed by filtration. The filtrate was evaporated to dryness under reduced pressure and the residue was diluted to 20 ml with EtOAc, washed with diluted HCI (10 ml). The insoluble material formed was filtered off and the organic phase was washed with H20 (5 ml), brine, dried over anhydrous MgS04, filtered and the filtrate evaporated to dryness. The residue was purified by flash column chromatography (FCC) (Si02, CH2CI2 and EtOAc, 9 : 1 ) to give the title compound (0.23 g; 67%) as a colourless solid. 1 H-NMR (CDCI3) 7.86 (m, 1 H); 7.49 - 7.55 (m, 2H); 6.72 (d, 1 H, J = 3 Hz) ; 4.8 (d, 2H, J = 3 Hz) ; 2.18 (broad s, 1 H);
  • 84
  • [ 2296-23-3 ]
  • [ 16466-97-0 ]
  • [ 16238-12-3 ]
YieldReaction ConditionsOperation in experiment
2-lodo-4-cynophenol (0.25 g, 1 mmol) and saccharin (0.1 g) in HMDSA (2 ml) was refluxed for 2 h under N2, until the solution became clear. The solvent was distilled off under reduced pressure and the residue was dissolved in anhydrous THF (2 ml). This was added to a solution made by mixing anhydrous ZnCI2 (0.3 g; 2.2 mmol) with 0.5 M 1 -propynyl magnesium bromide in THF (7.8 ml) in anhydrous THF (5 ml) at room temperature under N2 To it, Pd (PPh3)4 (0.15 g) was added at room temperature under N2 followed by catalytic amount of CuI. The mixture was stirred at room temperature for 3 h and quenched with saturated NH4CI solution. The mixture was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated and the residue was dissolved in 1 ,4-dioxane (4 ml) and 1 M TBAF in THF (0.3 ml) was added and this was stirred for 4 h at reflux. The solvent was distilled off and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.145 g, 91 %), as colourless solid. 1H-NMR (CDCI3) 7.78 (s, 1 H); 7.46 - 7.44 (m, 2H); 6.41 (bs, 1 H); 2.47 (s, 3H).
  • 85
  • [ 2296-23-3 ]
  • [ 16466-97-0 ]
  • [ 1304692-41-8 ]
YieldReaction ConditionsOperation in experiment
78% A suspension of the product of Step A (0.3 g; 1.22 mmol) in HMDSA (2 ml) and saccharine (0.1 g) was refluxed under N2 until reaction became homogenous (~ 30 min). After cooling to room temperature, the HMDSA was removed in vacuo and the residue was diluted to 4 ml with anhydrous THF. At the same time ZnCI2 (0.2 g; 1 .47 mmol) was heated to ~ 1 10 0C, in separate flask, in vacuo, cooled to room temperature under N2 and diluted to 4 ml with anhydrous THF. To it 0.5 M prop-1 -ynyl- magnesium bromide in THF (4.9 ml; 2.45 mmol) was added at room temperature and this was stirred for 10 min under N2 . To it a solution of silinated product of Step A was added, followed by Pd(PPh3)4 (0.1 1 g; 0.095 mmol) and CuI (0.05 g; 0.26 mmol). After stirring for 1 h at room temperature under N2, MeOH (5 ml) was added and solvents were removed under reduced pressure. The residue was diluted to 20 ml with EtOAc, washed with saturated NH4CI (2 x 5 ml), H2O (10 ml), brine, dried anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by FCC (SiO2, CH2CI2) to give title compound (0.16 g; 78%), as colourless solid. 1H-NMR (CDCI3 ) 2.14 (s, 3H); 6.26 (s, 1 H); 6.97 (d, 1 H, J = 8.5 Hz); 7. 46 (dd, 1 H, J = 2.1 Hz, 8.5 Hz); 7.57 (d, 1 H, 2.1 Hz).
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 2296-23-3 ]

Aryls

Chemical Structure| 1689-83-4

[ 1689-83-4 ]

4-Hydroxy-3,5-diiodobenzonitrile

Similarity: 0.97

Chemical Structure| 460746-47-8

[ 460746-47-8 ]

4'-Hydroxy-3'-iodo-[1,1'-biphenyl]-4-carbonitrile

Similarity: 0.95

Chemical Structure| 210962-75-7

[ 210962-75-7 ]

3-Hydroxy-4-iodobenzonitrile

Similarity: 0.94

Chemical Structure| 28177-77-7

[ 28177-77-7 ]

2-Hydroxy-3-iodobenzonitrile

Similarity: 0.90

Chemical Structure| 82504-06-1

[ 82504-06-1 ]

3-Iodo-4-methoxybenzonitrile

Similarity: 0.88

Iodides

Chemical Structure| 1689-83-4

[ 1689-83-4 ]

4-Hydroxy-3,5-diiodobenzonitrile

Similarity: 0.97

Chemical Structure| 460746-47-8

[ 460746-47-8 ]

4'-Hydroxy-3'-iodo-[1,1'-biphenyl]-4-carbonitrile

Similarity: 0.95

Chemical Structure| 210962-75-7

[ 210962-75-7 ]

3-Hydroxy-4-iodobenzonitrile

Similarity: 0.94

Chemical Structure| 28177-77-7

[ 28177-77-7 ]

2-Hydroxy-3-iodobenzonitrile

Similarity: 0.90

Chemical Structure| 82504-06-1

[ 82504-06-1 ]

3-Iodo-4-methoxybenzonitrile

Similarity: 0.88

Nitriles

Chemical Structure| 1689-83-4

[ 1689-83-4 ]

4-Hydroxy-3,5-diiodobenzonitrile

Similarity: 0.97

Chemical Structure| 460746-47-8

[ 460746-47-8 ]

4'-Hydroxy-3'-iodo-[1,1'-biphenyl]-4-carbonitrile

Similarity: 0.95

Chemical Structure| 210962-75-7

[ 210962-75-7 ]

3-Hydroxy-4-iodobenzonitrile

Similarity: 0.94

Chemical Structure| 28177-77-7

[ 28177-77-7 ]

2-Hydroxy-3-iodobenzonitrile

Similarity: 0.90

Chemical Structure| 82504-06-1

[ 82504-06-1 ]

3-Iodo-4-methoxybenzonitrile

Similarity: 0.88