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CAS No. : | 364-77-2 | MDL No. : | MFCD00153169 |
Formula : | C6H3FINO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ANPFMDLUEWNKIM-UHFFFAOYSA-N |
M.W : | 267.00 | Pubchem ID : | 2737347 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.94 |
TPSA : | 45.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.15 cm/s |
Log Po/w (iLOGP) : | 1.59 |
Log Po/w (XLOGP3) : | 2.5 |
Log Po/w (WLOGP) : | 2.76 |
Log Po/w (MLOGP) : | 2.22 |
Log Po/w (SILICOS-IT) : | 1.09 |
Consensus Log Po/w : | 2.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.41 |
Solubility : | 0.104 mg/ml ; 0.000391 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.11 |
Solubility : | 0.208 mg/ml ; 0.00078 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.01 |
Solubility : | 0.262 mg/ml ; 0.000982 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.26 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid Diazotization.Umsetzen der Diazoniumsalz-Loesung mit Kaliumjodid-Loesung; | ||
Stage #1: 2-nitro-4-fluoroaniline With toluene-4-sulfonic acid In water; acetonitrile at 10 - 15℃; Inert atmosphere; Stage #2: With potassium iodide; sodium nitrite In water; acetonitrile at 10 - 20℃; Inert atmosphere; | ||
With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In water; acetonitrile at 10 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With copper(l) iodide; cesium acetate In dimethyl sulfoxide at 90℃; for 12h; | |
With copper(l) iodide; cesium acetate In dimethyl sulfoxide at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With phenylmagnesium chloride In tetrahydrofuran at -60℃; for 0.0833333h; Stage #2: With Trimethyl borate In tetrahydrofuran at -60℃; for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran at -60℃; | |
Multi-step reaction with 2 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / water / -20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(l) iodide; cesium acetate In dimethyl sulfoxide at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 94 percent / CuI; CsOAc / dimethylsulfoxide / 12 h / 90 °C 2: 53 percent / aq. acetic acid; Fe / ethanol / 5 h / Heating | ||
Multi-step reaction with 2 steps 1: CuI; CsOAc / dimethylsulfoxide / 12 h / 90 °C 2: Fe; AcOH / aq. ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 94 percent / CuI; CsOAc / dimethylsulfoxide / 12 h / 90 °C 2: 53 percent / aq. acetic acid; Fe / ethanol / 5 h / Heating 3: 83 percent / NaBH3CN; glacial acetic acid / methanol / 20 °C / pH 6 | ||
Multi-step reaction with 3 steps 1: CuI; CsOAc / dimethylsulfoxide / 12 h / 90 °C 2: Fe; AcOH / aq. ethanol / Heating 3: NaBH3CN; AcOH / methanol / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hexamethylphosphoric acid triamide / 3 h / 90 - 100 °C 2: 90 percent / H2SO4 / H2O / 6 h / 160 - 170 °C | ||
Multi-step reaction with 2 steps 1: 1) 90-95 deg C, 2 h; 2) room temp., overnight 2: 90 percent / H2SO4 / H2O / 6 h / 160 - 170 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 8 percent / 1) 90-95 deg C, 2 h; 2) room temp., overnight 2: 91 percent / H2SO4 / H2O / 6 h / 95 - 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 130℃; for 9h; Inert atmosphere; | 4.1.2.1. Step 1. Methyl (2E)-3-(4-fluoro-2-nitrophenyl)acrylate (3) A solution of 4-fluoro-1-iodo-2-nitrobenzene 1 (Oakwood Products, 2.403 g, 9.00 mmol), triphenylphosphine (1.416 g, 5.40 mmol), dry Et3N (1.88 mL, 13.5 mmol), Pd(OAc)2 (303.1 mg, 1.35 mmol), and methyl acrylate (1.62 mL, 18.0 mmol) in dry DMF (24.0 mL) was stirred at 130 °C under N2 for 9 h. The reaction solution was cooled to room temperature, and concentrated in vacuo. The residue was partitioned between AcOEt/toluene solution (1:2, 60 mL) and H2O (50 mL). The organic layer was separated and the aqueous layer was extracted with AcOEt/toluene solution (1:3, 40 mL × 3). The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexane/AcOEt = 5:1) to afford 286.7 mg of the title product 3 in 14% yield as a yellow crystalline solid. 1H NMR (270 MHz, CDCl3) δ 8.07 (1H, d, 15.8 Hz), 7.78 (1H, dd, J = 8.07 Hz, J = 2.65 Hz), 7.68-7.63 (1H, m), 7.43-7.38 (1H, m), 6.34 (1H, d, J = 15.8 Hz), 3.84 (3H, s). |
287.1 Step 1. Step 1. Methyl trans-(4-Fluoro-2-nitro)cinnamate The title compound was prepared according to the procedure described in step 1 of Example 133 from 3-fluoro-6-iodonitrobenzene and methyl acrylate. 1H-NMR (CDCl3) δ: 8.67 (1H, d, 15.8 Hz), 7.78 (1H, dd, 8.07 Hz, 2.65 Hz), 7.68-7.63 (2H, m), 6.34 (1H, d, 15.8 Hz), 3.84 (3H, s). | ||
28.1 STEP 1. STEP 1. Methyl trans-(4-fluoro-2-nitro)cinnamate The title compound was prepared according to the procedure described in step 1 of Example 24 from 3-fluoro-6-iodonitrobenzene and methyl acrylate. 1H-NMR (CDCl3) δ: 8.67 (1H, d, 15.8Hz), 7.78 (1H, dd, 8.07Hz, 2.65Hz), 7.68-7.63 (2H, m), 6.34 (1H, d, 15.8Hz), 3.84 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h; | Into a round bottom flask was added <strong>[933768-06-0]3-ethynyl-2-fluoropyridine</strong> (0.3 g, 0.002 mol), 4- fluoro-l-iodo-2-nitrobenzene (0.675 g, 0.00253 mol), bis(triphenylphosphine)palladium(II) chloride (0.09 g, 0.1 mmol), copper(I) iodide (0.04 g, 0.2 mmol), and triethylamine (0.52 mL, 3.7 mmol) in N,N-dimethylformamide (4 mL). The reaction was stirred at room temperature for 2 hours. The reaction was extracted with ethyl acetate, and the combined organic extracts were washed with brine (3x), dried over MgSO4, and purified by column chromatography on silica gel (10% ethyl acetate 90% hexanes), to give 0.443 g of product. 1H nuMR (400 MHz, CDCl3): delta 8.44-8.50 (m, IH), 7.99-8.02 (m, IH), 7.79-7.90 (m, IH), 7.78-7.82 (m, IH), 7.37- 7.42 (m, IH), 7.23-7.29 (m, IH). MS [M+H]=261.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium carbonate In ethanol; toluene for 8h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With norborn-2-ene; trifuran-2-yl-phosphane; caesium carbonate; palladium dichloride In acetonitrile at 100℃; for 24h; sealed vial; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With copper(I) cyanide di(lithium chloride); phenylmagnesium chloride In tetrahydrofuran at -40℃; for 0.166667h; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; caesium carbonate In acetonitrile at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; caesium carbonate In acetonitrile at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With phenylmagnesium chloride; copper(l) cyanide; lithium chloride In tetrahydrofuran at -40℃; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at -40℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 9 h / 130 °C / Inert atmosphere 2.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux; Inert atmosphere 3.1: pyridine / dichloromethane / 24 h / 20 °C / Inert atmosphere 4.1: potassium carbonate / acetone / 46 h / 20 °C / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 9 h / 130 °C / Inert atmosphere 2.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux; Inert atmosphere 3.1: pyridine / dichloromethane / 24 h / 20 °C / Inert atmosphere 4.1: potassium carbonate / acetone / 46 h / 20 °C / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere 5.1: sodium hydroxide / tetrahydrofuran; methanol / 2.5 h / Inert atmosphere; Reflux 5.2: 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 9 h / 130 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol; water / 2 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 9 h / 130 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol; water / 2 h / Reflux; Inert atmosphere 3: pyridine / dichloromethane / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(l) iodide; 1,10-Phenanthroline; sodiumsulfide nonahydrate In acetic acid at 100℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With copper(l) iodide; 1,10-Phenanthroline; sodiumsulfide nonahydrate In acetic acid at 100℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; 1,10-Phenanthroline; sodiumsulfide nonahydrate In acetic acid at 100℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; caesium carbonate In acetonitrile at 110℃; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: cesium fluoride / dimethyl sulfoxide / 2 h / 20 °C 3.1: methanol / 0.08 h / 20 °C 3.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: cesium fluoride / dimethyl sulfoxide / 2 h / 20 °C 3.1: methanol / 0.08 h / 20 °C 3.2: 16 h / 50 °C 4.1: dichloro(2-picolinato)gold(III) / toluene / 2.5 h / 20 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: cesium fluoride / dimethyl sulfoxide / 2 h / 20 °C 3.1: methanol / 0.08 h / 20 °C 3.2: 16 h / 50 °C 4.1: dichloro(2-picolinato)gold(III) / toluene / 2.5 h / 20 °C / Reflux 5.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: cesium fluoride / dimethyl sulfoxide / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / water / -20 °C / Inert atmosphere 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,2-dimethoxyethane / 4 h / 100 °C 4.1: palladium diacetate; 1,10-Phenanthroline; molybdenum hexacarbonyl / 1,2-dichloro-ethane / 24 h / 120 °C / Schlenk technique; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / water / -20 °C / Inert atmosphere 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,2-dimethoxyethane / 4 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With phenylmagnesium chloride In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium iodide; In dimethyl sulfoxide; at 160℃; for 24h;Schlenk technique; | Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,21.8 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,37 mg of <strong>[394-01-4]2-nitro-4-fluorobenzoic acid</strong>, 45 mg of sodium iodide and 4 mL of dimethylsulfoxide. The reaction was heated at 160 C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases were concentrated to give 38.4 mg of 2-nitro-4-fluoroiodobenzene,The yield is 72%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide 2: iron; hydrogenchloride / water 3: potassium carbonate; N,N`-dimethylethylenediamine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide 2: iron; hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; | General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.166667h; Stage #2: phenylacetylene With copper(l) iodide for 6h; | ||
Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With bis-triphenylphosphine-palladium(II) chloride; triethylamine for 0.166667h; Stage #2: phenylacetylene With copper(l) iodide for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar and reflux condenser, was added ethyl 2-iodobenzoate (3j, 0.14 g 0.50 mmol), Cu2O (0.060 g, 0.42 mmol), and a DMF solution of 2-Zn (0.65 M, 1.54 mL, 1.0 mmol), and the mixture was stirred at 100 C for 24 h. After being cooled to room temperature, the resulting solution was subjected to a short pad of silica gel using hexanes as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography to provide the corresponding compound 4j (0.13 g, 0.48 mmol) in 96% yield as an yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With pyridine; copper(l) iodide; silver fluoride In N,N-dimethyl-formamide at 60℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; | 14 General procedure for the cross-coupling reaction of the silyl reagent with various iodoarenes A sealed tube was charged with CuI (0.19g, 1.0mmol, 2.5 equiv.), AgF (0.13g, 1.0mmol, 2.5 equiv.), pyridine (0.27mL, 8.3 equiv.), various iodoarenes (0.4mmol, 1.0 equiv.), triethyl(1,1,2,2-tetrafluorobut-3-en-1-yl)silane (4 : 0.19g, 0.8mmol, 2.0 equiv.) and DMF (3.2mL, 0.25M) in glove box. The sealed tube was brought under an atmosphere of argon and capped. The resulting mixture was stirred at 60°C for 16h, and then cooled room temperature. The resulting mixture was passed through short column. The eluent was concentrated in vacuo to give the crude materials, which were purified by silica gel column chromatography, leading to the desired coupling products |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92 %Spectr. | With potassium fluoride; trichloroisocyanuric acid In acetonitrile at 40℃; for 24h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: 2-ethynyl-1-nitrobenzene; 4-fluoro-1-iodo-2-nitrobenzene With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran Inert atmosphere; Stage #2: With trimethylsilylacetylene In tetrahydrofuran Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; tributyl-amine; sodium carbonate / water / 2 h / Inert atmosphere; Reflux 2: carbon monoxide; palladium diacetate; 3,4,7,8-Tetramethyl-o-phenanthrolin / N,N-dimethyl-formamide / 14 h / 100 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bis-triphenylphosphine-palladium(II) chloride; tributyl-amine; sodium carbonate In water for 2h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: 4-fluoro-1-iodo-2-nitrobenzene With phenylmagnesium chloride In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere; Stage #2: cyclobutanone In tetrahydrofuran at -40 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; potassium carbonate In pentan-1-ol at 140℃; for 6h; | 4.1 8-Chloro-11-(4-ethylpiperazin-1-yl)-1-fluoro-5H-dibenzo[b,e][1,4]diazepine (7a) (general procedure) General procedure: 2-Amino-6-fluorobenzoic acid (2a, 2.48g, 16mmol) in pentanol solution (50mL) was heated to 140°C. 4-Chloro-1-iodo-2-nitrobenzene (3a, 4.53g, 16mmol) was added to the reaction mixture, followed by K2CO3 (2.21g, 16.00mmol), and Cu powder (78mg, 1.22mmol). The reaction mixture was refluxed for 6h. After cooling down, the precipitated solid was filtered, dissolved in water, and acidified with aqueous HCl to form a yellow solid that was dried under vacuum. This crude solid compound 2-((4-chloro-2-nitrophenyl)amino)-6-fluorobenzoic acid (4a) (4.89g, 98.4% yield) was used for the next step without further purification. The above crude 4a (0.5g, 1.6mmol) was dissolved in methanol (10mL) and treated with NH4Cl (0.46g, 8mmol) and Zn (0.52g, 8mmol) at 5-10°C. The mixture was stirred at room temperature for 2h, and then filtered to remove solids. The filtrate was concentrated under vacuum to yield a green solid 5a. This solid was dissolved in dichloromethane (20mL) and treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCHCl) (0.92g, 4.8mmol, 3 equiv.). The reaction mixture was stirred at room temperature under argon for 12h, which then was concentrated to obtain a pale residue. The residue was treated with TiCl4 (1M in toluene) (1.9mL, 1.9mmol) and 1-ethylpiperazine (0.92g, 8mmol) in 1,4-dioxane (50mL) under argon. The mixture was heated to 100°C for 12h. After cooling down, the mixture was acidified with 1M aqueous HCl, and then extracted with ethyl acetate (EtOAc). The aqueous layer was basified with 1M aqueous NaOH, and then extracted with EtOAc. The organic layer was dried with Na2SO4, and concentrated for purification on a silica gel column to produce the pure product 7a as a yellow solid (0.225g, 39.4% yield over three steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | Stage #1: 4-fluoro-1-iodo-2-nitrobenzene; (1,1,2,2-tetrafluoro-4-(dimethylphenylsilyl)but-3-yn-1-yl)zinc bromide With copper(I) bromide In 1,4-dioxane; acetonitrile at 60℃; for 20h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; | 4.5. Typical procedure for Cu(I)-catalyzed cross-coupling reaction oforganozinc reagent 2-Zn with various iodoarenes with directing group General procedure: In a reaction vial equipped with a teflon-coated stirrer bar, ethyl 2-iodobenzoate (8b, 0.044 g 0.16 mmol), CuBr (0.007 g, 0.05 mmol),1,4-dioxane (1.0 mL), and a MeCN solution of 2-Zn (0.32 M, 1.0 mL,0.32 mmol) were added, and the mixture was stirred at 60 C for 20 h.After cooling to room temperature, the resultant was quenched withaqueous NH4Cl, and the whole sample was extracted with Et2O thrice.The organic layers were dried over anhydrous sodium sulfate andevaporated in vacuo. THF (0.5 mL) was added to the residue, which wasthen added dropwise to TBAF (1,0 M THF solution, 0.32 mL) at roomtemperature, and the mixture was stirred for 4 h. The reaction mixturewas quenched with water and extracted with Et2O thrice. The organiclayers were dried over anhydrous sodium sulfate. The dried organiclayer was concentrated in vacuo, and the residue was purified by silicagel column chromatography to give the corresponding adduct 10b in77% yield as a pale yellow oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydrogenchloride; iron(0) In ethanol; water monomer for 3h; Reflux; |
Tags: 364-77-2 synthesis path| 364-77-2 SDS| 364-77-2 COA| 364-77-2 purity| 364-77-2 application| 364-77-2 NMR| 364-77-2 COA| 364-77-2 structure
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H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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