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[ CAS No. 615-43-0 ] {[proInfo.proName]}

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Chemical Structure| 615-43-0
Chemical Structure| 615-43-0
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Product Citations

Mokhtarpour, Nazanin ; Sterling, Alyssa ; Garcia, Joshua J. , et al. DOI: PubMed ID:

Abstract: Reactive oxygen species (ROS) are a heterogeneous group of highly reactive ions and mols. derived from mol. oxygen (O2) which can cause DNA damage and lead to skin cancer. NADPH oxidase 1 (Nox1) is a major producer of ROS in the skin upon exposure to UV light. Functionally, Nox1 forms a holoenzyme complex that generates two superoxide mols. and reduces NADPH. The signaling activation occurs when the organizer subunit Noxo1 translocates to the plasma membrane bringing a cytochrome P 450, through interaction with Cyba. We propose to design inhibitors that prevent Cyba-Noxo1 binding as a topical application to reduce UV-generated ROS in human skin cells. Design started from an apocynin backbone structure to generate a small mol. to serve as an anchor point. The initial compound was then modified by addition of a polyethylene glycol linked biotin. Both inhibitors were found to be non-toxic in human keratinocyte cells. Further in vitro experiments using isothermal calorimetric binding quantification showed the modified biotinylated compound bound Noxo1 peptide with a KD of 2 nM. Both using isothermal calorimetric binding and MALDI (TOF) MS showed that binding of a Cyba peptide to Noxo1 was blocked. In vivo experiments were performed using donated skin explants with topical application of the two inhibitors. Experiments show that UV light exposure of with the lead compound was able to reduce the amount of cyclobutene pyrimidine dimers in DNA, a mol. known to lead to carcinogenesis. Further synthesis showed that the polyethylene glycol but not the biotin was essential for inhibition.

Keywords: Reactive oxygen species ; Apocynin ; UV ; Noxo1 ; Cyba ; Cyclobutane pyrimidine dimer ; CPD ; UV protection

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Product Details of [ 615-43-0 ]

CAS No. :615-43-0 MDL No. :MFCD00007680
Formula : C6H6IN Boiling Point : -
Linear Structure Formula :- InChI Key :UBPDKIDWEADHPP-UHFFFAOYSA-N
M.W : 219.02 Pubchem ID :11995
Synonyms :
2-Iodophenylamine

Calculated chemistry of [ 615-43-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.56
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 2.32
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 2.41
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.134 mg/ml ; 0.00061 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.685 mg/ml ; 0.00313 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.222 mg/ml ; 0.00101 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 615-43-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P280-P337+P313-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 615-43-0 ]

* 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 [ 615-43-0 ]

[ 615-43-0 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 615-43-0 ]
  • [ 148493-34-9 ]
  • 2-(2,6-Dichloro-pyridin-3-yl)-phenylamine [ No CAS ]
  • 2
  • [ 615-43-0 ]
  • [ 148493-34-9 ]
  • [ 26869-12-5 ]
  • 3
  • [ 615-43-0 ]
  • [ 60481-34-7 ]
YieldReaction ConditionsOperation in experiment
96% Step A. 2-Iodoaniline (16 g, 73 mmol) was suspended in concentrated hydrochloric acid (100 mL), and then cooled to 0 C. in an ice bath. Sodium nitrite (6 g, 87.6 mmol) in water (25 mL) was added slowly to reaction mixture and then reaction allowed to stir at 0 C. for 1.5 hours. In a separate flask, tin (II) chloride (84.7 g, 182.5 mmol) was dissolved in concentrated hydrochloric acid (12 mL) and added slowly over 30 minutes to reaction mixture. The resulting suspension was allowed to warm to room temperature and stirred for 14 h. The solid was filtered off, and allowed to dry to afford 1-(2-iodophenyl)hydrazine hydrochloride (19 g, 96%). 1H NMR (CDCl3, 300 MHz) delta 7.82 (dd, 1H, J=1.1, 7.7 Hz), 7.39 (dt, 1H, 1.2, 7.7 Hz), 6.96 (dd, 1H, J=1.1, 8.1 Hz), 6.82 (dt, 1H, J=1.1, 7.5) ppm. MS (ApCI) 275 (M++CH3CN+H).
60% With hydrogenchloride; tin(ll) chloride; sodium nitrite; at 0 - 20℃; for 19.5h; NaNO2 (3.0 g, 43.8 rnrnol) was slowly added to a suspension of 2-iodoaniline (8.0 g, 36.5 rnrnol) in concentrated HCI (40 rnL) at 0 oC. The reaction rnixture was stirred at 0 oC for 1.5 hrs. A solution of SnCI2 (17.3 g, 91.3 rnrnol) in 12 M HCI (10 rnL) was added at 0 oC. The reaction rnixture was allowed to warrn to r.t. and stirred for 18 hrs. The solid was collected by filtration and washed with H20 and dried under reduced pressure to give the title cornpound as a light brown solid (5.9 g, 60%).1H NMR (pprn)(DMSO-d6): 6.85 - 6.80 (1 H, rn), 7.06 (1 H, dd, J=1 .3, 8.3 Hz), 7.46 - 7.41 (1 H, rn), 7.64 (IH, s), 7.84 (IH, dd, J=1.4, 7.7 Hz), 10.30-10.16 (3H, rn)
32.4% With hydrogenchloride; tin(II) chloride dihdyrate; sodium nitrite; In water; at -5 - 20℃; for 24h; 2-Iodoaniline (10.0g, 45.7mmol) was added to a mixture of water (5.12 mL) and concentrated hydrochloric acid (11.5 mL) at 0 C. The solution was cooled to -5 C and a solution of sodium nitrite (3.50g, 49.2mmol) in water (5.1mL) was added dropwise and with stirring. While the solution was kept at 0 C, a solution of tin(II)-chloride dihydrate (23.2 g, 90.0 mmol) in 6 M hydrochloric acid (31.2 mL) was slowly added dropwise. After stirring for 24 h at room temperature, the mixture was made basic by adding 50% aqueous sodium hydroxide solution and was then extracted with diethyl ether (3 x 100mL). The combined organic layers were evaporated to a residual volume of 50 mL, dried (sodium sulfate) and filtered. While cooling with an ice bath, gaseous hydrogen chloride was bubbled through the diethyl ether solution. A precipitate formed, which was filtered off and was washed with diethyl ether to yield a beige solid (4.00 g, 32.4%); mp.: 163 - 167 C (Lit: 157 - 159 C [2]); IR (KBr): 3434, 3231, 2900, 2759, 2678, 1494, 741 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 10.33 (s, 3H), 7.79 (dd, 1H, 3JH,H= 7.8 Hz, 4JH,H = 1.4 Hz,), 7.38 (ddd, 1H, 3JH,H = 8.2 Hz, 3JH,H = 7.4 Hz, 4JH,H= 1.5 Hz), 7.02 (dd, 1H, 3JH,H = 8.2 Hz, 4JH,H = 1.4 Hz), 6.77 (ddd, 1H, 3JH,H = 7.8Hz, 3JH,H = 7.4 Hz, 4JH,H = 1.3 Hz); 13C NMR (150.9 MHz, DMSO-d6): delta = 144.9, 85.1 (quat C); 139.2, 128.9, 123.6, 114.1 (tert C); C6H8ClIN2 (270.50); calcd. C 26.64, H 2.98, N 10.36; found C 26.96, H 2.76, N 9.84; MS (EI): m/z = 234 ([M]+, 100), 219 ([M - NH]+, 26), 204 ([M - N2H2]+, 24).
  • 4
  • [ 615-43-0 ]
  • [ 141-97-9 ]
  • [ 53855-47-3 ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) iodide; 1H-tetrazol-1-ylacetic acid; caesium carbonate; In dimethyl sulfoxide; at 80℃; for 12h;Sealed tube;Catalytic behavior; General procedure: To a 10mL sealed tube was added CuI (0.05mmol), L4 (0.1mmol), ortho-iodo/bromoaniline (0.5mmol), beta-keto ester/beta-diketone (3.0mmol), Cs2CO3 (1.0mmol), and DMSO (1mL). The reaction mixture was reacted at 80C in a preheated oil bath for 12h (for ortho-iodoanilines) or 36h (for ortho-bromoanilines). The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether as the eluent) to afford the target products 3a-3s.
57.5% With copper(I) oxide; caesium carbonate; In water; dimethyl sulfoxide; at 100℃; for 16h;Inert atmosphere; Step 1: Ethyl 2-methyi-lH4ndoie-3-carboxylate.To a mixed solution of dimcthyl sulfoxide (100 mL) and water (34 mL), 24odobenzenamine (50 g, 228 mmol), ethyl 3-oxobutanoatc (35.6 g, 274 mmol), coppcr(i) oxide (3.3 g, 22.8 mmol) and cesium carbonate (75 g, 228 mmoi) was added. The mixture was stirred at 100C for 16 hours under nitrogen gas atmosphere. The reaction mixture was filtered through a pad of cehte. The filtrate was diluted with water and extracted with ethyl acetate, The organic phase was concentrated in vacuo, and then the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to afford the title compound as a light yellow solid (26.6 g, 57.5%), LCMS 204 (M + H).
15% With copper(I) oxide; caesium carbonate; In water; dimethyl sulfoxide; at 100℃; for 9h;Inert atmosphere; Ethyl 2-methyl-1H-indole-3-carboxylate. In a pyrex vial a mixture of 2-iodobenzenamine (3.0 g, 13.7 mmol), ethyl 3-oxobutanoate (2.0 g, 15.1 mmol), copper (I) oxide (0.2 g,1.4 mmol) and cesium carbonate (4.5 g, 13.7 mmol) were dissolved in DMSO:water (20 mL, 10:1) and heated at 100 C for 9 h under anitrogen atmosphere. The reaction mixture was filtered through a pad of Celite and the filtrate diluted with water. The aqueous layer was extracted with EtOAc (3X) and the combined organic layer was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silicagel chromatography (petroleum ether/EtOAc = 5:1) to afford ethyl 2-methyl-1H-indole-3-carboxylate as a light yellow solid (0.42 g,15% yield).
  • 5
  • [ 615-43-0 ]
  • [ 768-60-5 ]
  • [ 157869-15-3 ]
YieldReaction ConditionsOperation in experiment
93% General procedure: 2-iodoaniline (500.2 mg, 2.28 mmol, 1.0 equiv) was dissolved in Et3N (4.5 mL). The resulting solution was added with PdCl2(PPh3)2 (32.1 mg, 0.046 mol, 0.02 equiv) and CuI (17.4 mg, 0.091mmol, 0.04 equiv). The orange-yellow solution was degassed by bubbling with a stream of argon into the solution at room temperature for 30 min. After degassing, phenylacetylene (0.30 mL,279.0 mg, 2.73 mmol, 1.2 equiv) was added as a neat liquid into the solution via syringe. The resulting dark brown solution was allowed to stir at room temperature under argon atmosphere overnight. The reaction was quenched by addition of sat. aq. NH4Cl. The separated aqueousphase was extracted with EtOAc (3x times). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4, filtered and concentrated to a crude product. The crudeproduct was purified by SiO2 column chromatography eluting with 0-10% EtOAc-hexane to give 398.2 mg (90%) of 2-(phenylethynyl)aniline as an orange solid.
75% With sodium hydroxide; In toluene; at 130℃; for 72h; General procedure: To a stirred solution of the corresponding 2-iodoaniline (6, 1 mmol) in toluene (3 mL) under argon atmosphere were added Pd/CuO-Fe3O4 (50 mg), NaOH (400 mg, 10 mmol), and the corresponding alkyne (2, 1.5 mmol). The resulting mixture was stirred at 130 C until the end of reaction (see Table 6). The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The product was purified by chromatography on silica gel (hexane/ethyl acetate) to give the corresponding compounds 7. Yields are included in Table 6. Then, to a stirred solution of 7 (1 mmol) in toluene (4 mL) was added ZnBr2 (225 mg, 1 mmol). The resulting mixture was stirred at 130 C during 24 h. The mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to give the pure products 8 in quantitative yields. Physical and spectroscopic data for compounds 7 and 8, as well as literature for known compounds, follow.
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[2]Applied Organometallic Chemistry,2018,vol. 32
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[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 11835 - 11839
    Angew. Chem.,2013,vol. 125,p. 12051 - 12055,5
[5]New Journal of Chemistry,2018,vol. 42,p. 16886 - 16890
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[7]Liebigs Annales,1995,p. 775 - 780
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[10]Journal of Organic Chemistry,2019,vol. 84,p. 8121 - 8130
[11]Tetrahedron,2012,vol. 68,p. 1393 - 1400
[12]Synthesis,2009,p. 829 - 835
[13]ChemMedChem,2016,vol. 11,p. 2347 - 2360
[14]Tetrahedron Letters,2004,vol. 45,p. 35 - 38
[15]Organic Letters,2008,vol. 10,p. 4887 - 4889
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[17]Organic Letters,2011,vol. 13,p. 1098 - 1101
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    Angew. Chem.,2019,vol. 131,p. 8974 - 8978,5
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  • 6
  • [ 615-43-0 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
YieldReaction ConditionsOperation in experiment
98% With lithium hydroxide monohydrate; C24H23N3O3PdS; In N,N-dimethyl-formamide; at 130℃; for 20h; General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 molpercent of 5 in 2 mL N,N-dimethylformamide). The reaction mixture was stirred at 130 °C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 molpercent of catalyst 5 was applied.
86% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 30h; General procedure: The 25 mL RB-flask was charged with 2-iodoaniline (1 mmol), diphenylacetylene (1.5 mmol), K2CO3 (2 mmol) and PS-tsu-Pd(II) complex (3) (0.005 mmol) in DMF (2 mL). The reaction mixture was stirred at 100 °C for 30 h. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered to recover the catalyst. Then the experimental procedure was same as above.
  • 7
  • [ 932-16-1 ]
  • [ 615-43-0 ]
  • [ 94742-32-2 ]
  • 8
  • [ 1694-31-1 ]
  • [ 615-43-0 ]
  • [ 124-41-4 ]
  • [ 65417-22-3 ]
  • 9
  • [ 930-21-2 ]
  • [ 615-43-0 ]
  • [ 5755-07-7 ]
  • [ 682341-17-9 ]
  • 10
  • [ 4653-08-1 ]
  • [ 615-43-0 ]
  • 2''-iodophenyl-4-(2'-thienyl)-4-oxobutanamide [ No CAS ]
  • 11
  • [ 6342-80-9 ]
  • [ 615-43-0 ]
  • 1,2-dimethoxy-5,10-dihydro-indeno[1,2-b]indole [ No CAS ]
  • [ 62-53-3 ]
  • 12
  • [ 38222-83-2 ]
  • [ 615-43-0 ]
  • [ 143321-89-5 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic anhydride; In dichloromethane; water; Example 6B 2,2,2-Trifluoro-N-(2-iodophenyl)acetamide 2-Iodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl-4-methyl-pyridine (Aldrich, 1.23 g, 6 mmol) in CH2Cl2 (10 mL)at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3*10 mL). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70percent). 1H NMR (300 MHz, CD3OD) delta 7.07-7.12 (m, 1H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1H) ppm. MS (DCI): m/z 316 (M+H)+.
  • 13
  • [ 615-43-0 ]
  • [ 1007476-32-5 ]
  • [ 53855-47-3 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; In N,N-dimethyl-formamide; at 120℃; a) 2-Methyl-1H-indole-3-carboxylic acid ethyl ester A mixture of 2-iodo-phenylamine (44.30 g, 202 mmol), sodium salt of ethyl acetoacetate (42.1 g, 263 mmol), and Cu(I)I (50.1 g, 263 mmol) in DMF (200 mL) was stirred at 120 C. overnight. Then the reaction mixture was cooled to room temperature, then diluted with methyl tert-butyl ether (MTBE) and water, and concentrated ammonia was added to dissolve the solid, the two layers were separated, the water layer was back extracted with MTBE; all MTBEs were combined and washed with sat. NaCl aqueous solution, dried over anhydrous sodium sulfate, filtered, and concentrated sequentially. The residue was crystallized in hexanes/EtOAc, giving the desired product (10.84 g), the mother liquor was concentrated and purified on column to give an additional batch of product (4.76 g). The title compound, 1H NMR (200 MHz, CDCl3): delta (ppm)=8.32 (1H), 8.09 (m, 1H), 7.31-7.13 (m, 3H), 4.39 (q, 2H, J=6.8 Hz), 2.74 (s, 3H), 1.45 (t, 3H, J=6.8 Hz).
  • 14
  • [ 26510-52-1 ]
  • [ 615-43-0 ]
  • C16H14N2O2 [ No CAS ]
  • 15
  • [ 615-43-0 ]
  • [ 105-45-3 ]
  • [ 65417-22-3 ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; 1H-tetrazol-1-ylacetic acid; caesium carbonate; In dimethyl sulfoxide; at 80℃; for 12h;Sealed tube; General procedure: To a 10mL sealed tube was added CuI (0.05mmol), L4 (0.1mmol), ortho-iodo/bromoaniline (0.5mmol), beta-keto ester/beta-diketone (3.0mmol), Cs2CO3 (1.0mmol), and DMSO (1mL). The reaction mixture was reacted at 80C in a preheated oil bath for 12h (for ortho-iodoanilines) or 36h (for ortho-bromoanilines). The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether as the eluent) to afford the target products 3a-3s.
85% With cetyltrimethylammonim bromide; potassium carbonate; In water; at 50℃; for 3h;Green chemistry;Catalytic behavior; A mixture of the appropriate 1,3-dicarbonyl compound 3 (1.1equiv), 2-iodoaniline (1 equiv), CTAB (10 mol%), K2CO3 (1equiv), and magnetic catalyst (20 mg) in H2O (4 mL) was stirredat 50 C for 3 h then cooled to r.t. The catalyst was removed byusing an external magnet, and the solution was extracted withEtOAc (3 × 10 mL). The extracts were dried (MgSO4), filtered,and concentrated under vacuum to give a crude product thatwas purified by column chromatography.Methyl 2-Methyl-1H-indole-3-carboxylate (4a)Beige solid; yield: 160 mg (85%); mp 164-166 C. IR (KBr):3016, 1690, 1449, 1209, 10905 cm-1. 1H NMR (400 MHz, CDCl3):delta = 2.72 (s, 3 H), 3.93 (s, 3 H), 7.16-7.30 (m, 3 H), 8.08 (d, J= 7.7Hz, 1 H), 8.67 (br s, 1 H). 13C NMR (100 MHz, CDCl3): delta = 14.2,50.8, 104.3, 110.4, 121.2, 121.7, 122.3, 127.2, 134.5, 144.2,166.7.
  • 16
  • [ 615-43-0 ]
  • [ 6931-16-4 ]
  • 20
  • [ 615-43-0 ]
  • [ 3484-18-2 ]
  • 21
  • [ 615-43-0 ]
  • [ 65417-22-3 ]
  • 22
  • [ 615-43-0 ]
  • [ 776-41-0 ]
  • 23
  • [ 615-43-0 ]
  • [ 53855-47-3 ]
  • 24
  • [ 120-72-9 ]
  • [ 615-43-0 ]
  • [ 61798-24-1 ]
  • [ 473918-48-8 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; CuI; In toluene; Preparation of 1-(2-aminophenyl)indole at 80 C. Using the general procedure, indole (0.117 g, 1.00 mmol) was coupled at 80 C. with 2-iodoaniline (0.263 g, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N'-dimethyl-1,2-cyclohexanediamine (32 muL, 0.20 mmol, 20 mol %) and toluene (1.0 mL) to give the crude product. The above product was identified by comparison (GC) to a previously prepared sample and the GC yield was determined to be 92%.
  • 25
  • [ 615-43-0 ]
  • [ 75-36-5 ]
  • [ 7212-28-4 ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20℃; Acetyl chloride (6 mmol) was added dropwise to the mixture of 2-iodoaniline (5 mmol) and sodium hydroxide (13 mmol) in THF/H2O (1/1, 4 mL). Stirred the mixture at 0 C. for 2 h, and then at room temperature for overnight. The mixture was diluted with 10 mL water and extracted with diethyl ether 3 times. The combined organic layer was washed with water 3 times and brine. Dried over sodium sulfate, filtered, and removed solvent. The residue was then purified by column chromatography afforded white solid of 2-iodoacetanilide 68% yield. NMR
  • 27
  • [ 3314-30-5 ]
  • [ 615-43-0 ]
  • [ 26223-27-8 ]
  • 29
  • [ 766-98-3 ]
  • [ 615-43-0 ]
  • [ 1173153-20-2 ]
YieldReaction ConditionsOperation in experiment
91% General procedure: 2-iodoaniline (500.2 mg, 2.28 mmol, 1.0 equiv) was dissolved in Et3N (4.5 mL). The resulting solution was added with PdCl2(PPh3)2 (32.1 mg, 0.046 mol, 0.02 equiv) and CuI (17.4 mg, 0.091mmol, 0.04 equiv). The orange-yellow solution was degassed by bubbling with a stream of argon into the solution at room temperature for 30 min. After degassing, phenylacetylene (0.30 mL,279.0 mg, 2.73 mmol, 1.2 equiv) was added as a neat liquid into the solution via syringe. The resulting dark brown solution was allowed to stir at room temperature under argon atmosphere overnight. The reaction was quenched by addition of sat. aq. NH4Cl. The separated aqueousphase was extracted with EtOAc (3x times). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4, filtered and concentrated to a crude product. The crudeproduct was purified by SiO2 column chromatography eluting with 0-10% EtOAc-hexane to give 398.2 mg (90%) of 2-(phenylethynyl)aniline as an orange solid.
Reference: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 11835 - 11839
    Angew. Chem.,2013,vol. 125,p. 12051 - 12055,5
[2]Tetrahedron Letters,2018,p. 675 - 680
[3]Journal of Organic Chemistry,2010,vol. 75,p. 3412 - 3419
[4]Journal of Organic Chemistry,2019,vol. 84,p. 8121 - 8130
[5]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 565 - 569
[6]Tetrahedron Letters,2013,vol. 54,p. 2357 - 2361
[7]Journal of Organic Chemistry,2013,vol. 78,p. 10319 - 10328
[8]Organic Letters,2013,vol. 15,p. 5940 - 5943
[9]Chemical Communications,2014,vol. 50,p. 3024 - 3026
[10]European Journal of Organic Chemistry,2014,vol. 2014,p. 1622 - 1629
[11]RSC Advances,2014,vol. 40,p. 41561 - 41564
[12]Organic Letters,2014,vol. 16,p. 4924 - 4927
[13]Journal of Organic Chemistry,2016,vol. 81,p. 4412 - 4420
[14]Journal of Organic Chemistry,2016,vol. 81,p. 3994 - 4001
[15]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1373 - 1378
[16]Chemical Communications,2017,vol. 53,p. 8533 - 8536
[17]Organic Letters,2017,vol. 19,p. 3982 - 3985
[18]Journal of Organic Chemistry,2017,vol. 82,p. 8455 - 8463
[19]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6997 - 7007
[20]Organic Letters,2017,vol. 19,p. 6128 - 6131
[21]Journal of Organic Chemistry,2018,vol. 83,p. 10453 - 10464
[22]Advanced Synthesis and Catalysis,2019,vol. 361,p. 490 - 495
[23]Organic and Biomolecular Chemistry,2019,vol. 17,p. 2657 - 2662
[24]Angewandte Chemie - International Edition,2019,vol. 58,p. 8882 - 8886
    Angew. Chem.,2019,vol. 131,p. 8974 - 8978,5
[25]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5558 - 5564
[26]Chemical Communications,2020,vol. 56,p. 474 - 477
[27]Organic Letters,2020,vol. 22,p. 814 - 817
[28]Journal of Organic Chemistry,2020,vol. 85,p. 3224 - 3233
[29]Journal of Organic Chemistry,2020,vol. 85,p. 5379 - 5389
  • 30
  • [ 615-43-0 ]
  • [ 97628-92-7 ]
  • [ 1228230-77-0 ]
YieldReaction ConditionsOperation in experiment
24% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In acetonitrile; at 20℃; for 34h; To 1.0 g (4.57 mmol) iodoaniline in 30 mL acetonitrile were added 2.22 g (5.02 mmol) BOP, 1.78 g (4.57 mmol) azetidine-1 ,3-dicarboxylic acid monobenzyl ester (route 13, step a), 0.6 mL (4.57 mmol) triethylamine, and the mixture was stirred at room temperature for 16 hours. 0.6 mL (4.57 mmol) triethylamine was added and the mixture was stirred for 2 hours. 2.22 g (5.02 mmol) BOP was added and the mixture was stirred at room temperature for 16 hours. 30 mL 1 M aqueous Na2CO3 was added and the mixture was extracted with EtOAc (2 x 30 mL), the organic layers were combined, washed with 30 mL brine then dried with Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 7:3). Yield: 0.47 g (24percent of theory) Ci8H17IN2O3 (M= 436.25) predicted: Molecular ion (M+H)+: 437 observed: Molecular ion (M+H)+: 437 HPLC-MS: 1.39 minutes (Method D)
  • 31
  • [ 1123-99-5 ]
  • [ 615-43-0 ]
  • [ 206-80-4 ]
  • 32
  • [ 873-73-4 ]
  • [ 615-43-0 ]
  • [ 221910-19-6 ]
YieldReaction ConditionsOperation in experiment
76% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Schlenk technique; General procedure: In a typical reaction, PdCl2(PPh3)2 (88 mg, 0.125 mmol), CuI (24 mg, 0.125 mmol) and THF (5 ml) were placed in an oven-dried, 2-neck RB flask. To this suspension, 2-iodoaniline (5.47 mg, 2.5 mmol) and triethylamine (702 mul, 5.0 mmol) were added. The reaction mixture was degassed by bubbling with argon for 15 min. Phenylacetylene (300 mul, 2.75 mmol) was then added, and the reaction mixture stirred at RT. After complete consumption of the 2-iodoanilines (~2 h, by TLC), the reaction mixture was filtered through celite, and the solvent rotary evaporated to obtain the crude product which was purified by silica gel (60-120 mesh) column chromatography using ethylacetate/ hexane (1:9, v/v) as eluent to give pure 2-phenylethynylaniline, 2a (400 mg, 83%).
With palladium/copper catalyst;Inert atmosphere; General procedure: All reagents were used as received without further purification.2-Alkynylanilines 1a-i were prepared by palladium/copper-catalysedSonogashira coupling reactions of 2-iodoanilines with terminalalkynes according to a literature method.31 The Fe3O4SiO2-bipy-AuCl3 complex was prepared according to our previous procedure.42The gold content was determined to be 0.62 mmol g-1. All reactionswere carried out under Ar in oven-dried glassware with magneticstirring. 1H NMR spectra were recorded on a Bruker Avance 400 (at400 MHz) spectrometer with TMS as an internal standard using CDCl3as the solvent. 13C NMR spectra were recorded on a Bruker Avance 400(at 100 MHz) spectrometer using CDCl3 as the solvent. HRMS spectrawere recorded on a quadrupole-time of flight Bruker MicroTOF-QII mass spectrometer equipped with an ESI and APCI source. Goldcontent was determined using ICP-AES on an Atomscan16 instrument(TJA Corporation).
  • 33
  • [ 3364-80-5 ]
  • [ 615-43-0 ]
  • [ 1848-82-4 ]
  • 34
  • [ 3453-33-6 ]
  • [ 615-43-0 ]
  • [ 1345838-83-6 ]
  • 35
  • [ 615-43-0 ]
  • [ 4491-33-2 ]
  • piperidin-1-yl(quinolin-2-yl)methanone [ No CAS ]
  • 36
  • [ 14369-81-4 ]
  • [ 615-43-0 ]
  • [ 53855-47-3 ]
  • 37
  • [ 3453-33-6 ]
  • [ 615-43-0 ]
  • [ 1374581-08-4 ]
  • 38
  • [ 615-43-0 ]
  • [ 21575-91-7 ]
  • [ 1373169-28-8 ]
  • 39
  • [ 5683-31-8 ]
  • [ 615-43-0 ]
  • 3-trimethylsilanyl-propynoic acid (2-iodo-phenyl)-amide [ No CAS ]
  • 40
  • [ 1003-31-2 ]
  • [ 615-43-0 ]
  • [ 873056-71-4 ]
  • 42
  • [ 615-43-0 ]
  • [ 7211-39-4 ]
  • [ 1197953-47-1 ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 3.0h; Step 1 : synthesis of compound 1To a solution of 2-iodoaniline ( 1.0 eq) and dimethylphosphine oxide (1.1 eq) in DMF were added potassium phosphate ( 1.1 eq) and palladium acetate/Xantphos (catalytic). The reaction was stirred at 150 °C for 3 hours and cooled to room temperature. The solvent was evaporated and the residue was worked up with DCM/water. The crude product was purified with a column(EtOAc/MeOH 10: 1 ) to give 1 as a brown solid (80percent yield).
80% With potassium phosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 3.0h; To a solution of 2-iodoaniline (1.0 eq) and dimethylphosphine oxide (1.1 eq) in DMF were added potassium phosphate (1.1 eq) and palladium acetate/Xantphos (catalytic). The reaction was stirred at 150 °C for 3 hours and cooled to room temperature. The solvent was evaporated and the residue was worked up with DCM/water. The crude product was purified with a column (EtOAc/MeOH 10:1) to give 1 as a brown solid (80percent yield).
80% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 3.0h; Synthesis of 1 (0791) (0792) To a solution of 2-iodoaniline (1.0 eq) and dimethylphosphine oxide (1.1 eq) in DMF were added potassium phosphate (1.1 eq), palladium acetate/Xantphos (catalytic). The reaction was stirred at 150° C. for 3 hours and cooled to room temperature. The solvent was evaporated and the residue was worked up with DCM/water. The crude product was purified with a column (EtOAc/MeOH 10:1) to give 1 as a brown solid (80percent yield).
79.96% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In water; N,N-dimethyl-formamide; at 110 - 125℃; for 3.0h;Inert atmosphere; The 2 - iodo aniline (990.01 g, 4. 52 muM, 1 equivalent) and dimethyl phosphine oxide (690 g, 5.2 muM, 1.15 equiv), K3PO4(0.594 g, 0.226 muM, 0.05 wt) in DMF (5.5 L, ) and water (0.55 L) in, the reaction mixture is under the protection of nitrogen, heated to 110 - 125 ° C and stirring 3 hours. LCMS and TLC (PE: EA = 10: 1, DCM: MeOH = 10: 1 ) Display the completion of reaction. The mixture is filtered and concentrated, wherein the DMF is removed, the resulting residues of ethyl acetate (2 L) dilution. Then adding HC / EA (4 M, 2 L) make the product into a salt , There are a large quantity of solid precipitate, stirring to make it uniform dispersion, the concrete filtering, the filter cake is used which acetone (0.4 L x 3) washing, and drying solid, to obtain the target compound (817 g, yield 79.96percent IS) AS Yellow Solid
62.15% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100℃; for 16.0h;Inert atmosphere; 2-iodoaniline solution (12.50 g, 57.07 mmol) and Example 1J (5.35 g, 68.49 mmol), K3PO4 (14.54 g, 68.49 mmol), Xantphos (660.44 mg, 1.14 mmol) and palladium acetate ( 256.26 mg, 1.14 mmol) in DMF (80mL), the reaction mixture was stirred under nitrogen and heated to 100 deg. C and stirred for 16 hours. LCMS (DCM: methanol = 10: 1) showed the reaction was complete. The mixture was filtered and concentrated and the resulting residue was diluted with aqueous HCl (1N, 80mL), the pH is adjusted to about 2, and the resulting mixture was filtered. The filtrate (100mL × 2) and extracted with the DCM, the aqueous layer was separated, and washed with aqueous sodium bicarbonate to adjust the pH to about 9, and (200mL × 2) and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by recrystallization (the PE: ethyl acetate = 5: 1) to give the title compound (6.00 g, 35.47 mmol, 62.15percent yield) as a white solid.
62.15% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 120℃; for 6.0h;Inert atmosphere; To a solution of 2-iodoaniline (1.0g, 4.57mmol, 1.Oeq) in dimethylformamide (lOmL) were added compound 128.1 (0.463g, 5.94mmol, Oeq) and potassium phosphate (1.937g, 9.14mmol, 2. Oeq). The reaction mixture was degassed for 10 min under argon atmosphere, and palladium acetate (0.103g, 0.457mmol, O. leq) and 4,5-Bis(Diphenylphosphino)-9,9-dimethylxanthene (0.529g, 0.914mmol, 0.2eq) were added. Reaction mixture was again degassed for 10 min and stirred at 120°C for 6h. After completion of reaction, reaction mixture was transferred into water and extracted with ethyl acetate. Organic layer was combined, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 3percent methanol in dichloromethane as eluent to obtain 128.2. (0.48g, 62.15percent). MS(ES): m/z 170.16 [M+H]+
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 0.12℃; [00366] A mMure of 2iodoaniHne (66 g, 0.393 moL 1.0 eq.), dimethyl phosphine oxide (36.4 g, 0466 meL 1.19 eq.), potasshim phosphate (92.4 g. 0.423 mol, 1.1 eq.), paNadk1m(H) acetate (4.56 g, 002 mol, 005 eq), and Xantphos (11.6g, 0.02 mel. 0.05 eq.) in DMF (700 mL) was stirred at ?120° C for ?6 h. The color of the mixture turned dark brown. Upon cooling to rt, celite (30 g) was added to the mixture. The mixture was then filtered and the filter cake was rinsed with EtOAc (2 x 250 mL). The filtrate was then concentrated in vacuo to afford a residue. [00367] Another batch of (2..aminophenyl)dimethylphosphine oxide was synthesized at the same scale as performed above, and the residue obtained from both batches were combined and purified as discussed below.[00368] To the combined residues was added EtOAc (1 L), and the resulting mixture was stirred at rt for ?1 h. The mixture was filtered, and the collected residue was washed with EtCAc (2 x 250 mL), The combined filtrate was dried over sodium sulfate, filtered and concentrated in vacuo to afford an oil. The resulting oil was dissolved in a mixture of water / concentrated hydrochloric acid (1 .2 L / 300 mL) with agitation at rt, and stirred for 30 mm. The resulting mixture was filtered, and the collected residue was washed with aqueous hydrochloric acid (10percent, 300 mL). The combined aqueous filtrate was washed with EtOAc (2 x I L washes, followed by a 500 mL wash). The aqueous layer was cooled in an ice bath (less than 10° C internal mixture temperature) and the pH of the solution was adjusted to?12 (as determined by pH paper) by adding aqueous sodium hydroxide (30percent w/w), while maintaining an internal solution temperature of less than 20° C throughout the addition. The resulting solution was extracted with IPA?DCM (1/3 v/v, 4 x I L), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford a viscous oil, which crystallized upon standing at rt. The resulting solids were triturated with EtOAc/heptane (1/10 v/v, 2 x 150 mL) to afford (2aminophenyl)dimethylphosphine oxide as a light brown solid.
With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100℃; for 6.0h;Inert atmosphere; 2-iodoaniline (17.5 g, 79.9 mmol) and dimethyl phosphine oxide (6.9 g, 88.5 mmol) were added,Palladium acetate (0.3 g, 1.3 mmol), Xantphos (0.77 g, 1.3 mmol),N,N-diisopropylethylamine (22.7 g, 175.8 mmol), DMF (50 mL),Magnetic stirring. Under nitrogen protection, heat to 100°C for 6 hours,The 2-iodoaniline consumption was monitored by thin layer chromatography. Cool to room temperature2,4,5-trichloropyrimidine (17.5 g, 95.9 mmol) was added and the reaction was heated to 75°C for 6 hours.The reaction was complete by thin layer chromatography. Cool to room temperature, add water 300mL,Adjust pH to 5 with 5percent hydrochloric acid and extract with ethyl acetate (100 mL x 3).Wash with sodium bicarbonate solution (100 mL), wash with saturated sodium chloride solution (100 mL × 2),Dry over anhydrous sodium sulfate. It is filtered with suction and concentrated to give a crude brown solid.Recrystallization with ethyl acetate/petroleum ether (volume ratio 1:2) gave an almost white solid 17g.Yield 67.3percent.

  • 44
  • [ 615-43-0 ]
  • [ 14401-51-5 ]
  • [ 1019-85-8 ]
YieldReaction ConditionsOperation in experiment
84% With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine; In N,N-dimethyl-formamide; at 140℃; for 16h;Inert atmosphere; General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product.
  • 45
  • [ 2879-20-1 ]
  • [ 615-43-0 ]
  • [ 1396341-76-6 ]
  • 46
  • [ 615-43-0 ]
  • [ 3080-99-7 ]
  • 48
  • [ 7533-40-6 ]
  • [ 615-43-0 ]
  • [ 1449421-01-5 ]
YieldReaction ConditionsOperation in experiment
73% With copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; In dimethyl sulfoxide; at 20℃; for 14h;Schlenk technique; Inert atmosphere; General procedure: Into a flame dried Schlenk tube containing a magnetic stir bar was added aryliodide (1.0mmol), amino alcohol (1.1mmol), Cs2CO3 (652mg, 2.0mmol; or 977mg, 3.0mmol for entries 1-5 in Table 5, which employ ephedrine hydrochloride salt) and CuI (9.5mg, 0.05mmol). Under an atmosphere of argon, DMSO (2mL) and 2,2,6,6-tetramethylheptane-3,5-dione (21.0muL, 0.1mmol) or indole-2-carboxylic acid (0.1mmol) were added and the reaction mixture was stirred at room temperature for 14h. After addition of ethyl acetate (15mL) and brine (5mL), the organic layer was separated and the aqueous layer extracted with ethyl acetate (3×20mL). The combined organic layer was dried over anhydrous Na2SO4 before passing it through a short pad of silica gel. The filtrate was concentrated and purified via flash column chromatography to afford the corresponding arylated product
  • 49
  • [ 615-43-0 ]
  • [ 421552-12-7 ]
  • C14H10FIN2 [ No CAS ]
  • 50
  • [ 615-43-0 ]
  • [ 52784-31-3 ]
  • [ 1449379-49-0 ]
  • 51
  • [ 615-43-0 ]
  • [ 108238-09-1 ]
  • [ 35883-09-1 ]
YieldReaction ConditionsOperation in experiment
12%Chromat. With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry; derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.
  • 52
  • [ 53590-49-1 ]
  • [ 2769-64-4 ]
  • [ 615-43-0 ]
  • [ 62-23-7 ]
  • C27H24ClIN4O4 [ No CAS ]
  • 53
  • [ 1003-31-2 ]
  • [ 615-43-0 ]
  • [ 3878-18-0 ]
  • 54
  • [ 455-37-8 ]
  • [ 615-43-0 ]
  • [ 324-15-2 ]
  • 55
  • [ 615-43-0 ]
  • [ 103-81-1 ]
  • [ 621-72-7 ]
  • 56
  • [ 615-43-0 ]
  • [ 768-60-5 ]
  • [ 221910-19-6 ]
  • 57
  • [ 53590-49-1 ]
  • [ 615-43-0 ]
  • C15H10ClIN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In dichloromethane; for 4h;Inert atmosphere; Reflux; General procedure: A mixture of 1H-indole-2-carbaldehyde (1 mmol, 145.16 mg, 1.0 equiv) and 2-iodoaniline (1.1 mmol, 240.93 mg, 1.1 equiv) was dissolved in anhydrous dichloromethane (20 mL), trifluoroacetic acid (0.2 mmol, 15 muL, 0.2 equiv) was added under nitrogen, and the resulting mixture was heated to reflux for 4 h. Then the solvent was evaporated, and the residue was dissolved in anhydrous methanol (15 mL), NaBH4 (4 mmol, 151 mg, 4.0 equiv) was added portionwise. After addition, the mixture was stirred for 30 min and concentrated under vacuum, the reaction mixture was washed with a saturated solution of NH4Cl, and then extracted with ethyl acetate. The organic extracts were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography (petroleum ether/EtOAc = 16:1 as eluent) to give 1a. White solid (299.4 mg, 86%).
  • 58
  • [ 2785-98-0 ]
  • [ 615-43-0 ]
  • [ 926583-68-8 ]
YieldReaction ConditionsOperation in experiment
30% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Example 17 N-(2-iodophenyl)-2,5-dimethoxybenzamide 2-iodoaniline (286 mg, 1.31 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCI, 418 mg, 2.1 mmol), 1-hydroxybenzotriazole (HOBT, 250 mg, 1.85 mmol) and <strong>[2785-98-0]2,5-dimethoxybenzoic acid</strong> (200 mg, 1.09 mmol) are dissolved into methylene chloride (8 mL) under nitrogen, 4-methylmorpholine (NMM, 400 muL, 1.85 mmol) is added thereto, and the reaction mixture is agitated for 16 hours at room temperature. The reaction progress and result are checked by TLC. After completing the reaction, the reaction mixture is concentrated under reduced pressure. After extracting the reaction mixture with ethyl acetate and water, the organic layer is dried with dry magnesium sulfate, followed by filtering. The filtrate is concentrated under reduced pressure and the concentrate is purified by column chromatography (EA:n-hHex=1:2) to obtain 75 mg of the target compound (yield: 30%). 1H NMR (300 MHz, CDCl3-d) delta ppm 10.31 (br s, 1H) 8.50 (d, J=4.86 Hz, 1H) 7.85 (m, 2H) 7.37 (m, 1H) 7.08 (m, 1H) 7.01 (m, 1H) 6.86 (m, 1H) 4.08 (s, 3H) 3.86 (s, 3H)
  • 59
  • [ 615-43-0 ]
  • [ 1006-47-9 ]
  • 60
  • [ 615-43-0 ]
  • [ 75418-74-5 ]
  • [ 1596359-76-0 ]
  • 61
  • [ 615-06-5 ]
  • [ 615-43-0 ]
  • [ 1198328-89-0 ]
  • 62
  • [ 615-43-0 ]
  • [ 5350-41-4 ]
  • [ 883-93-2 ]
  • 63
  • [ 615-43-0 ]
  • [ 64085-52-5 ]
  • N-(5-bromo-2-iodo-phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% 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.
  • 64
  • [ 615-43-0 ]
  • [ 121-44-8 ]
  • [ 101066-61-9 ]
  • C14H9ClN2 [ No CAS ]
  • 65
  • [ 615-43-0 ]
  • [ 63555-50-0 ]
  • methyl 3-[[(2-iodophenyl)amino]sulfonyl]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With pyridine; dmap; at 20℃; for 48h; General procedure: Typically a mixture of 2-iodoaniline (1.1 g, 5.0 mmol), 4-DMAP (30 mg, 0.24 mmol) and the arylsulfonyl chloride (6.0 mmol) in pyridine (10 mL) was stirred at room temperature for 2 days. The pyridine was removed in vacuo, the residue dissolved in CH2Cl2 (25 mL) washed with saturated aqueous CuSO4 (2x20 mL) and water (20 mL), dried over MgSO4, filtered, the solvent removed in vacuo and the residue purified by column chromatography or crystallisation.
  • 66
  • [ 615-43-0 ]
  • [ 26638-43-7 ]
  • methyl 2-[[(2-iodophenyl)amino]sulfonyl]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With pyridine; dmap; at 20℃; for 48h; General procedure: Typically a mixture of 2-iodoaniline (1.1 g, 5.0 mmol), 4-DMAP (30 mg, 0.24 mmol) and the arylsulfonyl chloride (6.0 mmol) in pyridine (10 mL) was stirred at room temperature for 2 days. The pyridine was removed in vacuo, the residue dissolved in CH2Cl2 (25 mL) washed with saturated aqueous CuSO4 (2x20 mL) and water (20 mL), dried over MgSO4, filtered, the solvent removed in vacuo and the residue purified by column chromatography or crystallisation.
  • 67
  • [ 201230-82-2 ]
  • [ 615-43-0 ]
  • [ 373-88-6 ]
  • [ 149-73-5 ]
  • 3-(2,2,2-trifluoroethyl)quinazolin-4(3H)-one [ No CAS ]
  • 68
  • [ 615-43-0 ]
  • [ 405520-68-5 ]
  • 2'-amino-N,N-dimethyl[1,1'-biphenyl]-4-carboxamide [ No CAS ]
  • 69
  • [ 615-43-0 ]
  • [ 89787-12-2 ]
  • [ 1402547-19-6 ]
  • 70
  • [ 615-43-0 ]
  • [ 205383-87-5 ]
  • 73
  • [ 75230-49-8 ]
  • [ 615-43-0 ]
  • [ 101125-32-0 ]
  • 74
  • [ 615-43-0 ]
  • [ 2567-29-5 ]
  • N-([1,1'-biphenyl]-4-ylmethyl)-2-iodoaniline [ No CAS ]
  • 75
  • [ 615-43-0 ]
  • [ 178946-89-9 ]
  • 76
  • [ 185-72-8 ]
  • [ 615-43-0 ]
  • 4-(((2-iodophenyl)amino)methyl)tetrahydro-2H-pyran-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With lithium perchlorate; In acetonitrile; at 90℃; for 18h; General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50% EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80%) as a colourless syrup.
  • 77
  • [ 185-72-8 ]
  • [ 615-43-0 ]
  • 2',3,3',4,5',6'-hexahydrospiro[benzo[b][1,4]oxazine-2,4'-pyran] [ No CAS ]
  • 78
  • [ 56146-83-9 ]
  • [ 615-43-0 ]
  • methyl 2-[N-(2-iodophenyl)sulfamoyl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; In acetonitrile; A solution of methyl(chlorosulfonyl)acetate (2a) (5.18 g, 30.0 mmol) in anhydrous MeCN (30.0 mL) wasslowly added to a stirred solution of 2-iodaniline (1a) (7.23 g, 33.0 mmol) and pyridine (2.84 g, 35.9mmol) in anhydrous MeCN (75 mL) at 10 C within 30 min. The reaction mixture was then warmed up to 30 C and stirred for another 1 h. Water (250 mL) was then added, the mixture was acidified with conc. HCl to pH 2, and extracted with CH2Cl2 (3 × 75 mL). The combined organic fractions were washed with 5% HCl (2 × 50 mL), brine (50 mL), and dried over anhydrous Na2SO4. The solvents were removed, and the crude product was purified by recrystallization from a mixture of Et2O and hexane to give 3 (8.44 g, 72%)
  • 79
  • [ 615-43-0 ]
  • [ 107-18-6 ]
  • [ 1006-47-9 ]
  • 80
  • [ 615-43-0 ]
  • [ 101251-09-6 ]
  • [ 3366-62-9 ]
  • 81
  • [ 259209-21-7 ]
  • [ 615-43-0 ]
  • [ 7320-51-6 ]
  • 82
  • [ 259209-21-7 ]
  • [ 615-43-0 ]
  • 2′-amino-5-methyl-[1,1′-biphenyl]-2-ol [ No CAS ]
  • 83
  • [ 259209-20-6 ]
  • [ 615-43-0 ]
  • [ 1225945-77-6 ]
  • 84
  • [ 259209-20-6 ]
  • [ 615-43-0 ]
  • [ 391-46-8 ]
  • 85
  • [ 615-43-0 ]
  • [ 244-69-9 ]
  • 86
  • [ 615-43-0 ]
  • [ 89694-46-2 ]
  • 2'-chloro-5'-methoxy-[1,1'-biphenyl]-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; water; at 130℃; for 1h;Microwave irradiation; General procedure: Substituted 2-iodoaniline 1 (1.0 eq.), substituted phenylboronicacid 2 (1.2 eq.), K2CO3 (3.0 eq.), tetrabutylammonium bromide (0.1eq.), PdCl2(dppf) (0.1 eq.) and dioxane/H2O (9:1) (0.5 M) wereadded to a 10 mL microwave-vial. The vial was sealed with a capand placed in a Cem Discover-microwave cavity. After irradiation at130 C for 1 h and subsequent cooling, the solvent was removed invacuo. The residue was taken up into EtOAc (30 mL) and washedonce withwater and brine. The organic layerwas dried over MgSO4,filtered, and concentrated. The crude product was purified by flashcolumn chromatography using 0e10percent EtOAc/petroleum benzine togive the biphenylamine product 3a-3aa.
  • 87
  • [ 444666-39-1 ]
  • [ 615-43-0 ]
  • 2'-chloro-5'-fluoro-[1,1'-biphenyl]-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; water; at 130℃; for 1.0h;Microwave irradiation; General procedure: Substituted 2-iodoaniline 1 (1.0 eq.), substituted phenylboronicacid 2 (1.2 eq.), K2CO3 (3.0 eq.), tetrabutylammonium bromide (0.1eq.), PdCl2(dppf) (0.1 eq.) and dioxane/H2O (9:1) (0.5 M) wereadded to a 10 mL microwave-vial. The vial was sealed with a capand placed in a Cem Discover-microwave cavity. After irradiation at130 C for 1 h and subsequent cooling, the solvent was removed invacuo. The residue was taken up into EtOAc (30 mL) and washedonce withwater and brine. The organic layerwas dried over MgSO4,filtered, and concentrated. The crude product was purified by flashcolumn chromatography using 0e10% EtOAc/petroleum benzine togive the biphenylamine product 3a-3aa.
  • 88
  • [ 2745-26-8 ]
  • [ 615-43-0 ]
  • [ 1569-98-8 ]
YieldReaction ConditionsOperation in experiment
72% With copper(II) acetate monohydrate; sulfur; sodium hydroxide; In dimethyl sulfoxide; at 130℃; for 24h;Sealed tube; Inert atmosphere; General procedure: A mixture of o-iodoaniline (0.5 mmol, 1 equiv), arylacetic acid (0.6 mmol), elemental sulfur (1.5mmol), Cu(OAc)2·H2O (20 mmol%), and NaOH (1.0 mmol) in DMSO (3 mL) was put into a sealed pressure vessel (25 mL) containing a magnetic stirring bar. The tube was purged with nitrogen three times, and then capped and stirred in a preheated oil bath at 130 C for 24 h. The reaction mixture then cooled to room temperature and extracted with ethyl acetate (3x10 mL), the organic layer was washed with saturated NaCl (2x10 mL), dried over anhydrous Na2SO4, evaporated under vacumm and then purified by silica gel column chromatography by using petroleum ether and ethyl acetate (PE:EA=200:1) as eluent.
  • 89
  • [ 615-43-0 ]
  • [ 116632-14-5 ]
  • [ 19029-32-4 ]
YieldReaction ConditionsOperation in experiment
70.5% With 18-crown-6 ether; copper; caesium carbonate; In 1,2-dichloro-benzene; for 12h;Inert atmosphere; Reflux; In a 500ml three-vial bottle,Under nitrogen protection,In order, 0.04 mol of intermediate 2-2 was added0.05mol 2-iodoaniline,0.05mol Cs2CO3,0.004mol Cu powder, 0.004mol 18 crown 6,200ml o-dichlorobenzene mixing,Heat to reflux,Insulation reaction for 12 hours,Sampling point board,Shows no intermediate 2-2 remaining,The reaction is complete; naturally cool to room temperature,filter,The filtrate was evaporated under reduced pressure until no fractions were found.Over neutral silica gel column,Intermediate 2-3 is obtained,HPLC purity 99.2%,Yield 70.5%;
  • 90
  • [ 615-43-0 ]
  • [ 1197953-47-1 ]
YieldReaction ConditionsOperation in experiment
60.42% With palladium diacetate; dimethyl phosphine oxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 2.0h;Inert atmosphere; A mixture of 2-iodoaniline (1.5g, 6.85mmol, 1.Oeq), dimethyl phosphine oxide (0.590g, 7.53mmol, 1.leq), Potassium phosphate (1.6g, 7.53mmol, 1.leq) in dimethylformamide (l5mL) was degassed by argon for 20mm. Xantphos (0.397g, 0.685mmol, 0.leq), Palladium(II) acetate (0.153g, 0.685mmol, 0.leq,) was added into reaction mixture and again degassed by argon for 30mm. Further reaction mixture was stirred at 150°C for 2h. Upon completion, reaction mixture was transferred into water and extracted with10percent MeOH in CH2C12. Organic layers were combined, dried over Na2SO4 and concentrated in vacuo to obtain crude product. This was purified by column chromatography and compound was eluted in 5percent MeOH in CH2C12 to obtain pure 242.1 (0.700g, 60.42 percent). MS(ES): m/z 170.16 [M+H].
  • 92
  • [ 615-43-0 ]
  • [ 1483-56-3 ]
  • C14H8BrF3INO [ No CAS ]
  • 93
  • [ 615-43-0 ]
  • [ 1483-56-3 ]
  • 11-methylene-10b-phenyl-8-(trifluoromethyl)-10b,11-dihydro-6H-isoindolo[2,1-a]indol-6-one [ No CAS ]
  • 94
  • [ 615-43-0 ]
  • [ 4892-02-8 ]
  • [ 3159-07-7 ]
  • 95
  • [ 1017684-61-5 ]
  • [ 615-43-0 ]
  • [ 65417-22-3 ]
  • 96
  • [ 615-43-0 ]
  • [ 23326-27-4 ]
  • [ 65417-22-3 ]
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