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CAS No. : | 41825-73-4 | MDL No. : | MFCD00047826 |
Formula : | C8H10BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YOSJCQJJIHEUKA-UHFFFAOYSA-N |
M.W : | 200.08 | Pubchem ID : | 170579 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.48 |
TPSA : | 26.02 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) : | -5.63 cm/s |
Log Po/w (iLOGP) : | 2.19 |
Log Po/w (XLOGP3) : | 2.66 |
Log Po/w (WLOGP) : | 2.66 |
Log Po/w (MLOGP) : | 2.88 |
Log Po/w (SILICOS-IT) : | 2.7 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.126 mg/ml ; 0.000631 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.86 |
Solubility : | 0.278 mg/ml ; 0.00139 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.67 |
Solubility : | 0.0428 mg/ml ; 0.000214 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.17 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss.-alkal. Stannit-Loesung; | ||
(deamination); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With hydrogen bromide; oxygen; 2-methylpyridinium nitrate; In water; at 90℃; for 6h; | General procedure: A mixture of substrate 1 or 3 (5 mmol), HBr (5.5 mmol,40% aqueous solution), and 2-methylpyridinium nitrate (5.5 mmol) was stirred in a reaction flask equipped with a condenser and an O2 balloon at the temperature given inTables 1 and 2. Thin layer chromatography (TLC) and gaschromatography (GC) were used to monitor the progress ofthe reaction. Purification and identification of the productFor 2a-2l. Ten milliliters of saturated Na2CO3 aqueoussolution was added at the end of the reaction, and the resultingmixture was extracted with 20 mL EA three times. Thecombined organic layer was washed with water and driedover Na2SO4; the concentrated residue was purified by columnchromatography (silica gel, petroleum ether (PE): EAfrom 200:1 to 80:1) to afford product 2. |
57% | 2-Bromo-4,6-dimethylaniline To a solution of 50.0 g (0.413 mol) of 2,4-dimethylaniline in 1500 cm3 of glacial acetic acid, 21.2 ml (65.6 g, 0.410 mol) of bromine was added dropwise with vigorous stirring over ca. 20 minutes. This mixture was stirred for 2 hours at 40 C. The precipitate that formed was filtered off, washed with 50 ml of acetic acid, and dried in air. The resulting white solid was added to a solution of 100 g of potassium hydroxide in 400 ml of water. This mixture was stirred for 30 minutes. The crude product was extracted with 3×100 ml of dichloromethane. The combined extracts were dried over Na2SO4 and evaporated to dryness. Fractional distillation gave yellowish liquid, bp 83-85 C./1 mm Hg. Yield 46.9 g (57%). Anal. calc. for C8H10BrN: C, 48.02; H, 5.04. Found: C, 48.15; H, 5.12. 1H NMR (CDCl3): delta 7.11 (s, 1H, 3-H), 6.79 (s, 1H, 5-H), 3.88 (br.s, 2H, NH2), 2.18 (s, 3H, 4-Me), 2.15 (s, 3H, 6-Me). 13C NMR (CDCl3): delta 139.7, 130.3, 130.2, 128.4, 123.4, 110.8, 20.0, 18.3.2-Bromo-4,6-dimethylaniline To a solution of 50.0 g (0.413 mol) of 2,4-dimethylaniline in 1500 cm3 of glacial acetic acid 21.2 ml (65.6 g, 0.410 mol) of bromine was added dropwise while vigorously stirring for ca. 20 min. This mixture was stirred for 2 h at 40 C. The precipitate formed was filtered off, washed with 50 ml of acetic acid, and dried in air. Then, this white solid was added to a solution of 100 g of potassium hydroxide in 400 ml of water. This mixture was stirred for 30 min. The crude product was extracted with 3×100 ml of dichloromethane. The combined extract was dried over Na2SO4 and evaporated to dryness. Fractional distillation gave a yellowish liquid, bp 83-85 C./1 mm Hg. Yield 46.9 g (57%). Anal. calc. for C8H10BrN: C, 48.02; H, 5.04. Found: C, 48.15; H, 5.12. 1H NMR (CDCl3): delta 7.11 (s, 1H, 3-H), 6.79 (s, 1H, 5-H), 3.88 (br.s, 2H, NH2), 2.18 (s, 3H, 4-Me), 2.15 (s, 3H, 6-Me). 13C NMR (CDCl3): delta 139.7, 130.3, 130.2, 128.4, 123.4, 110.8, 20.0, 18.3. | |
57% | With bromine; acetic acid; at 40℃; for 2.33333h; | 21.2 ml (65.6 g, 0.410 mol) of bromine were added dropwise, while vigorously stirring, over ca. 20 minutes to a solution of 50.0 g (0.413 mol) of 2,4-dimethylaniline in 1500 cm3 of glacial acetic acid. This mixture was stirred for 2 hours at 400C. The precipitate that formed was filtered off, washed with 50 ml of acetic acid, and dried in air. Then, this white solid was added to a solution of 100 g of potassium hydroxide in 400 ml of water. This mixture was stirred for 30 minutes. The crude product was extracted with 3 x 100 ml of dichloromethane. The combined extract was dried over Na2SO4 and evaporated to dryness. Fractional distillation gave a yellowish liquid, bp 83-85C/l mm Hg. Yield 46.9 g (57%).Anal. calc. for C8H10BrN: C, 48.02; H, 5.04. Found: C, 48.15; H, 5.12.1H NMR (CDCl3): delta 7.11 (s, IH, 3-H), 6.79 (s, IH, 5-H), 3.88 (br.s, 2H, NH2), 2.18 (s, 3H, 4-Me), 2.15 (s, 3H, 6-Me). <n="125"/>13C NMR (CDCl3): delta 139.7, 130.3, 130.2, 128.4, 123.4, 110.8, 20.0, 18.3. |
40% | With dihydrogen peroxide; copper diacetate; potassium bromide; In water; at 20℃; for 2h; | 0.5 mmol of 2,4-dimethylaniline (1e) was added to 4 mL of water,Add 0.125 mmol copper acetate to it,1.0mmol potassium bromide,1.0mmol hydrogen peroxide,Reaction at room temperature for 2 hours,After the reaction is over,Saturated aqueous NaCl solution was added to the reaction solution.Extract with ethyl acetate,The organic layer was dried over anhydrous magnesium sulfate.filter,60 C evaporated to dryness,That is, a crude product of the compound represented by the formula (2e) is obtained.The crude product of the compound represented by the formula (2e) is subjected to silica gel column chromatography.Ethyl acetate and petroleum etherThe product ratio is 1:The solution of 6 is mobile phase.The TLC tracked the elution with an Rf of 0.3-0.5.The eluent collected is reducedPress to remove the solvent,dry,The compound of the formula (2e) was obtained as 40 mg of pure product.Yield 40%. |
46.9 g (57%) | With potassium hydroxide; bromine; In water; acetic acid; | 2-Bromo-4,6-dimethylaniline 21.2 ml (65.6 g, 0.410 mol) of bromine were added dropwise, while vigorously stirring, over ca. 20 minutes to a solution of 50.0 g (0.413 mol) of 2,4-dimethylaniline in 1500 cm3 of glacial acetic acid. This mixture was stirred for 2 hours at 40 C. The precipitate that formed was filtered off, washed with 50 ml of acetic acid, and dried in air. Then, this white solid was added to a solution of 100 g of potassium hydroxide in 400 ml of water. This mixture was stirred for 30 minutes. The crude product was extracted with 3*100 ml of dichloromethane. The combined extract was dried over Na2SO4 and evaporated to dryness. Fractional distillation gave a yellowish liquid, bp 83-85 C./1 mm Hg. Yield 46.9 g (57%). Anal. calc. for C8H10BrN: C, 48.02; H, 5.04. Found: C, 48.15; H, 5.12. 1H NMR (CDCl3): delta 7.11 (s, 1H, 3-H), 6.79 (s, 1H, 5-H), 3.88 (br.s, 2H, NH2), 2.18 (s, 3H, 4-Me), 2.15 (s, 3H, 6-Me). 13C NMR (CDCl3): delta 139.7, 130.3, 130.2, 128.4, 123.4, 110.8, 20.0, 18.3. |
With N-Bromosuccinimide; In acetonitrile; at 0 - 20℃; for 3.5h; | General procedure: 60 mL CH3CN in a 500 mL round bottom flask was cooled down to 0C by ice bath and para-substituted aniline (28.0 mmol) was added to it. N-bromosuccinimide (5.1 g, 28.7 mmol) was then added in portions during 1.5 h to this stirring solution. After stirring further at ambient temperature for 2 h, the volatiles were removed in vacuo and the residue was redissolved in 100 mL CH2Cl2. The CH2Cl2 solution was filtered through Celite and washed with 3×50 mL H2O and then 50 mL of saturated NaCl (aq) to remove the succinimide by-product. The volatiles were then removed in vacuo to yield a brown liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With triethylamine In 1,4-dioxane at 25℃; for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With N-chloro-succinimide; dimethylsulfide; trifluoroacetic acid In dichloromethane -20 deg C to RT; RT, 3 h; | |
53% | In methanol for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride; sodium nitrite at 0℃; for 0.5h; Stage #2: With potassium iodide In water at 20℃; for 12h; Further stages.; | |
77% | Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride In water Inert atmosphere; Schlenk technique; Stage #2: With sodium nitrite In water Inert atmosphere; Schlenk technique; Stage #3: With potassium iodide In water Inert atmosphere; Schlenk technique; | |
60% | Gattermann reaction; |
60% | Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride In water at 80℃; for 0.5h; Stage #2: With sodium nitrite In water at 0 - 10℃; for 0.5h; Stage #3: With potassium iodide In water at 10 - 20℃; for 12h; | Compound 137: A mixture of dimethyl-bromoaniline (0.05 mol), H20 (100mL), and 37% aq.HCI(100mL) was heated to 8000 while stirring. The mixture was stirred 30 mm followed by cooling to 000 on an ice/water bath.NaNO2(0.055 mol) was added maintaining the internal temperature below 10°C. The resulting clear, orange solution was stirred at 0°C for 30 mm followed by addition ofKl(0.055mo1) as a solution in H20 (50 mL) keeping the internal temperature below 10°C. The black suspension was allowed to reach room temperature and stirred for 12h. The suspension was extracted with DCM, washed with water and brine, dried over with Mg2SO4, cncentration of the solution in vacuo gave a brown residue that was purified by column chromatography (hexane) to afford compound 137 (60%) as a yellow orange oil.137:1H-NMR (0D2012, 250 MHz): 7.34 (s, 1H), 7.03 (s, 1H), 2.54 (s, 3H), 2.28 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.5% | With triethylamine In dichloromethane at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In ethyl acetate at 80℃; for 0.5h; | |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.666667h; | 2.2 General procedure for the preparation of N-(2-bromophenyl)-N-methylacylamides General procedure: The procedure consists of two steps. First, to a stirred, cooled (0-5°C) solution of 2-bromoaniline (2.190g, 10mmol) and Et3N (1.113g, 1.55ml, 11mmol) in 20ml of dry THF, a solution of an appropriate acyl chloride (10mmol) in 5ml of dry THF was added dropwise within 10min. Then the ice bath was removed and the mixture was stirred vigorously for 30min at room temperature. Then, solid Et3NHCl was filtered off and washed with THF (3×5ml). The resulting organic fractions were combined and THF was removed under reduced pressure to yield crude amides. Recrystallization from hexane/CHCl3 and drying in vacuum afforded the analytically pure intermediate compounds: N-(2-bromophenyl)acylamides. In the second step, to a stirred suspension of NaH (0.132g; 5.5mmol) in 5ml of dry THF at 0°C the respective amide (5mmol) dissolved in 10ml of THF was added dropwise within 10min. The reaction mixture was stirred until the solution became clear (30min, hydrogen gas evolved), and the solution of MeI (0.923g; 0.405ml; 6.5mmol) in 5ml of THF was added dropwise within 10min. The solution was warmed up to room temperature and stirred for 3-8h. Then, the reaction mixture was quenched with water (30ml). The resulting solution was extracted with ethyl acetate (3×20ml). Combined organic layers were washed with brine (1×20ml) and dried over Na2SO4. Ethyl acetate was removed under reduced pressure to give crude 1a-r. Recrystallization from hexane and drying in vacuum afforded analytically pure compounds 1a-r. In the case of (1n) and (1o), the same procedure was conducted but instead of MeI, ethyl bromide and benzyl bromide were respectively used. In the case of (1p), 2-bromopyridin-3-amine was used instead of 2 bromoaniline. In the case of (1a-Cl) and (1a-I), the same procedure was conducted but instead 2-bromoaniline, 2-chloro- and 2-iodoaniline were respectively used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; benzene Heating; | |
59% | With palladium diacetate; diisopropylamine In water at 100℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium phosphate; 2C32H41O4P*Pd(2+)*2Cl(1-) In toluene at 110℃; for 16h; Inert atmosphere; | 4.9 General procedure for Suzuki-Miyaura coupling run in organic solvent General procedure: A dried and argonated Schlenk tube containing a magnetic stir bar was charged with aryl halide (1mmol), arylboronic acid (1.5mmol), 3mL of appropriate solvent, base (3mmol), and catalyst (see Table 1). The flask was evacuated, backfilled with argon and placed in to the oil bath (kept at appropriate temperature) on a magnetic stirrer for 16h. After that 20mL of water was added to the reaction mixture and product was extracted with methylene chloride (3×10mL), combined organic layer was dried over MgSO4, filtered, solvent was evaporated and the product was isolated by column chromatography. Yields: 64-99%. |
82.3% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 72h; Schlenk technique; Inert atmosphere; Reflux; | |
65% | With {bis[N,N′-(4-methyl-2-sec-phenethylphenyl)imino]-2,3-butadiene}dichloropalladium; potassium carbonate In water at 20℃; for 12h; |
62% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; benzene for 72h; Heating; | |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 12h; Reflux; | ||
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 88.9 % Chromat. 2: 7.6 % Chromat. | With 8-quinolinol; copper(l) chloride In diethylene glycol dimethyl ether at 90 - 95℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-aminopyridine; copper(l) chloride In methanol; diethylene glycol dimethyl ether at 85℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium carbonate In 1,2-dimethoxyethane; water at 95℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium carbonate In 1,2-dimethoxyethane; water at 95℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52% 2: 3% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 68% 2: 2.5% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 61% 2: 3.4% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 2% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 94 percent / aq. Na2CO3; Pd(PPh3)4 / benzene; ethanol / Heating 2: 31 percent / p-toluenesulfonic acid / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 62 percent / aq. Na2CO3; Pd(PPh3)4 / benzene; ethanol / 72 h / Heating 2: 95 percent / p-toluenesulfonic acid / benzene / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84 percent / ethyl acetate / 0.5 h / 80 °C 2: 91 percent / Pd(OAc)2; 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl; K3PO4 / toluene / 14 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 84 percent / ethyl acetate / 0.5 h / 80 °C 2: 91 percent / Pd(OAc)2; 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl; K3PO4 / toluene / 14 h / 90 °C 3: 95 percent / Pd(OAc)2; molecular sieves 3 Angstroem; Cu(OAc)2 / O2 / toluene / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 69.5 percent / Et3N / CH2Cl2 / 15 h / 20 °C 2.1: BH3*Me2S / toluene / 18 h / 95 °C 2.2: aq. HCl / toluene / pH 3 2.3: 43 percent / Et3N / CH2Cl2 / 7 h / 20 °C 3.1: 98 percent / CuI; NaI; N,N'-dimethylethylenediamine / dioxane / 48 h / 115 - 120 °C 4.1: aq. HCl / tetrahydrofuran / 2 h / 0 - 20 °C 4.2: 90.6 percent / HCO2H / 22 h / 120 - 125 °C 5.1: 78 percent / KF / Pd(OAc)2 / methanol / 72 h / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 69.5 percent / Et3N / CH2Cl2 / 15 h / 20 °C 2.1: BH3*Me2S / toluene / 18 h / 95 °C 2.2: aq. HCl / toluene / pH 3 2.3: 43 percent / Et3N / CH2Cl2 / 7 h / 20 °C 3.1: 98 percent / CuI; NaI; N,N'-dimethylethylenediamine / dioxane / 48 h / 115 - 120 °C 4.1: aq. HCl / tetrahydrofuran / 2 h / 0 - 20 °C 4.2: 90.6 percent / HCO2H / 22 h / 120 - 125 °C 5.1: 84 percent / KF / Pd(OAc)2 / methanol / 72 h / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dmap In dichloromethane at 20℃; for 18h; | 2.1 To a solution of the N-Boc-piperidine-4-carboxylic acid (4.00 g, 17.5 mmol) in CH2C12 (80 mL) stirred under N2 at room temperature was added oxalyl chloride (1.50 mL, 17.2 mmol) followed by DMF (68 uL, 0.88 mmol). The reaction was stirred for 1 h and Et3N (5.5 mL, 40 mmol) was added followed by the addition of 2-bromo-4, 6-dimethyl aniline (2.60 mL, 20.8 mmol) and 4- (dimethylamino) pyridine (210 mg, 1.72 mmol). After stirring for 18 h at room temperature, the reaction mixture was diluted with CHUCK (100 mL) and washed sequentially with HC1 (1N aq. , 3 x 100 mL) and NaHCO3 (sat. aq. , 100 mL). The organic layer was dried with MgS04, filtered, and concentrated. Purification by silica gel chromatography (15% ethyl acetate in hexanes) gave 4- (2-bromo-4, 6-dimethyl-phenylcarbamoyl)-piperidine-1-carboxylic acid tert- butyl ester (2.75 g, 6.94 mmol, 40% yield) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In acetonitrile; at 150℃; for 0.166667h; | lc N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamide.; 2-Bromo-4,6-dimethyl-aniline (600 mg) and (4-fluoro-phenyl)-acetyl chloride (543 mg) were dissolved in acetonitrile (6 mL) and heated to 150 C for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0 0C, the product filtered off and washed with cold acetonitrile (50 mL) affording 665 mg (66% yield) of the title compound as a white solid. LC-MS (m/z) 337 (MH+); tR = 2.93, (UV, ELSD) 90%, 98%. 1H NMR (500 MHz, DMSOd6): 2.05 (s, 6H), 2.25 (s, 3H), 3.63 (s, 2H), 7.05 (b, IH), 7.15 (dt, 2H), 7.32 (b, IH), 7.40 (dt, 2H), 9.67 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium t-butanolate In toluene at 215℃; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium t-butanolate In toluene at 215℃; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium t-butanolate In toluene at 215℃; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With caesium carbonate In toluene at 100℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate In toluene at 100℃; for 8h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate; triethylamine In methanol; ethyl acetate; toluene | 23.1 Step 1: Step 1: Synthesis of 3,5-dimethyl-6-phenanthridinamine Added together 2-cyanophenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) to a 125 mL of a 95/5 mixture of toluene/methanol. The solvents were degassed and the reaction mixture heated to reflux for 48 hours. After cooling, the reaction mixture was vacuum filtered and the organics evaporated and crude product was purified using silica gel column chromatography treated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants. The pure product was collected and concentrated to give 3,5-dimethyl-6-phenanthridinamine (9.1 g, 82% Yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 2-bromo-4,6-dimethylaniline With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 1h; Stage #2: chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane In tetrahydrofuran; hexane at 20℃; | 7; 8 N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under an argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80° C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172° C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): δ 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe'), 0.06 (s, 3H, SiMeMe'). 13C NMR (CDCl3): δ 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under and argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80° C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise for ca. 1 hour while vigorously stirring to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172° C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): δ 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe'), 0.06 (s, 3H, SiMeMe'). 13C NMR (CDCl3): δ 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: 2-bromo-4,6-dimethylaniline With n-butyllithium In tetrahydrofuran; hexanes at -50 - 20℃; for 2h; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In tetrahydrofuran; hexanes at 0 - 20℃; | 10 Under an argon atmosphere, to a solution of 13.9 g (69.5 mmol) of2-bromo-4,6-dimethylaniline in 200 ml of THF, 27.9 ml of 2.5 M (69.5 mmol) "BuLi in hexanes were added at -5O0C. This mixture was stirred for 2 hours at ambient temperature. The resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 15.0 g (69.5 mmol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-l-yl)silane in 100 ml of THF at O0C. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue 100 ml of toluene were added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 180-184°C/0.5 mm Hg. Yield 20. I g (77%).Anal. calc. for C19H28BrNSi: C, 60.03; H, 7.46. Found: C, 60.25; H, 7.40.1H NMR (CDCl3): δ 7.15 (s, IH3 3-H in phenyl), 6.82 (s, IH, 5-H in phenyl), 3.10 (br.s, IH, 1-H in Cp), 2.95 (br.s, IH, NH), 2.22 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.01 (s, 6H, 2,5-Me in Cp), 1.83 (s, 6H, 3,4-Me in Cp), 0.15 (s, 6H, SiMe2).13C NMR (CDCl3): δ 140.8, 136.5, 132.7, 131.1, 130.8, 130.7, 130.3, 118.4, 56.3, 20.5, 20.1, 14.5, 11.3, -0.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride In acetonitrile at -10 - 20℃; for 0.25h; Stage #2: With sodium nitrite In acetonitrile for 0.5h; Cooling; Stage #3: N-methylaniline With potassium carbonate In water; acetonitrile at -10 - 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride In acetonitrile at -10 - 20℃; for 0.25h; Stage #2: With sodium nitrite In acetonitrile for 0.5h; Cooling; Stage #3: N-methyl-N-(4-methoxyphenyl)amine With potassium carbonate In water; acetonitrile at -10 - 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2Na(1+)*CuC6H4(NCHC6H3OO3S)2(2-)=CuC6H4(NCHC6H3ONaO3S)2; tetrabutylammomium bromide; potassium carbonate In water at 120℃; for 30h; | 3. General procedure for Synthesis of phenazines General procedure: 2-iodoaniline (0.5 mmol) or 2-bromoaniline (0.5 mmol), complex 1 (0.05mmol), K2CO3 (1 mmol), (n-Bu)4NBr (0.1 mmol) and water (10 mL) were added to a sealed tube. The reaction mixture was stirred at 120oC for 30 h, then cooled to room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the solvent was then removed under reduced pressure. The product was finally obtained by column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium tetrachloropalladate(II); N-ethyl-N,N-diisopropylamine; catacxium A In toluene at 100℃; for 16h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With toluene-4-sulfonic acid In toluene for 3h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: 2-bromo-4,6-dimethylaniline; phenyl isocyanate In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: molybdenum hexacarbonyl With potassium phosphate; palladium diacetate; catacxium A In toluene at 120℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With N-ethyl-N,N-diisopropylamine; sodium iodide In toluene at 120℃; for 15h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With lithium hydroxide monohydrate; C24H23N3O3PdS In N,N-dimethyl-formamide at 130℃; for 20h; regioselective reaction; | General procedure for the Larock indolization of 2-iodoaniline and 2-bromoanilines 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 mol% 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 mol% of catalyst 5 was applied. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.2% | In isopropyl alcohol at 80℃; for 0.5h; Microwave irradiation; | 4.2.6. General procedure for the synthesis of 5,6,7-trimethoxy-Naryl-4-aminoquinazolines (6a-6z) General procedure: In the MW method, a mixture of 4-chloro-5,6,7-trimethoxyquinazoline (3.0 mmol) and aryl amine (3.0 mmol) in 2-propanol (10 mL) was stirred for 3 min and then reacted under MW at 100 W and 80 °C for 20 min. Upon reaction completion as monitored by thin-layer chromatography (TLC), the solvent was removed under reduced pressure. The residue was dissolved with methanol or chloroform and purified by TLC (petroleum ether/ethylacetate, 1:2, V:V). The target compound was eluted from the silica gel with ethyl acetate to give the title compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.18 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In hexane; N,N-dimethyl-formamide at 10 - 30℃; for 16h; Inert atmosphere; | 1-40 <Preparation of the Compound of the Formula 3-1> Under nitrogen atmosphere, at RT, 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex 2.04 g, cesium carbonate 48.8 g and the compound of the formula (5-1) 10 g were dissolved in N,N-dimethylformamide 125 ml. To the resulting solutions was added dropwise triethylborane (32.5 ml) (1.0M hexane solution) and the resulting mixtures were stirred at RT under nitrogen atmosphere for 16 hours. The reaction solutions were filtered through Celite and then to the filtrates was added water and the resulting mixtures were extracted with tert-butyl methyl ether, and the organic layers were washed with saturated saline and dried over anhydrous magnesium sulfate. The resulting organic layers were concentrated under reduced pressure and subjected to a silica gel column chromatography (eluates, ethyl acetate hexane=1:19→1:9) to give the compound of the formula (3-1) 3.18 g. [0932] 1H NMR (CDCl3) [0933] δ ppm: 6.78 (2H, s), 3.49 (2H, s), 2.51 (2H, q), 2.23 (3H, s), 2.16 (3H, s), 1.24 (3H, t) |
3.18 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In hexane; N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 1-40 Production of Compound Represented by Formula 3-1 Production Example 1-40 Production of Compound Represented by Formula (1-41) Production of Compound Represented by Formula 3-1 2.04 g of 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride-dichloromethane complex, 48.8 g of cesium carbonate, and 10 g of the compound represented by Formula (5-1) were dissolved in 125 ml of N,N-dimethylformamide at room temperature in a nitrogen atmosphere. 32.5 ml (1.0 M hexane solution) of triethylborane was added dropwise to the obtained solution, followed by stirring at room temperature for 16 hours in a nitrogen atmosphere. After the reaction liquid was filtered using Celite (registered trademark), water was added to the filtrate, the resultant product was extracted with tert-butyl methyl ether, and the organic layer was washed with a saturated saline solution, and dried over anhydrous magnesium sulfate. The obtained organic layer was concentrated under reduced pressure, and the resultant product was subjected to silica gel column chromatography (eluent, ethyl acetate:hexane=1:19→1:9), whereby 3.18 g of the compound represented by Formula (3-1) was obtained. 1H NMR (CDCl3) δ ppm: 6.78 (2H, s), 3.49 (2H, s), 2.51 (2H, q), 2.23 (3H, s), 2.16 (3H, s), 1.24 (3H, t) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate at 20℃; for 36h; | General procedure for synthesis of S16- S23 General procedure: To a homogenous solution of S7 (20 mmol) in dioxane (60 mL) was added K2CO3 (21 mmol) and anilines S2/S4/S10-S15 (21 mmol) and allowed to stir at room temperature for 36 h. Solvents were evaporated and water was added, extracted with EtOAc (3 x100 mL), organic layers were washed with NaHCO3, brine and water, dried and evaporated to get white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In methanol; toluene for 24h; Inert atmosphere; Reflux; | General procedure: To a stirred solution of the corresponding aniline (1 mmol),Cs2CO3 (2 mmol), and Pd(PPh3)4 (5 mol%) in toluene (20mL) at reflux and under nitrogen atmosphere, a solution ofN-Boc-pyrrol-2-yl boronic acid17 (1 mmol) in a mixture oftoluene (10 mL) and MeOH (3 mL) was added over 7 h. Themixture was stirred at reflux for 17 h, cooled, and the MeOHwas removed under reduced pressure. To the resultanttoluene suspension H2O (30 mL) was added, and the layerswere separated. The water layer was extracted with CH2Cl2(3 × 25 mL; or EtOAc for compound 5), the combinedorganic extracts were washed with H2O (30 mL), dried overMgSO4, filtered, and the solvent was evaporated underreduced pressure. The residue was purified by columnchromatography on silica gel using a suitable eluent asindicated below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In toluene at 90℃; for 33h; Inert atmosphere; Schlenk technique; | |
68% | In toluene at 90℃; for 33h; Schlenk technique; | 1-1 (2-bromo-4,6-dimethylphenyl)carbamic acid tertbutyl ester In 100mL Schlenk flask 2-bromo-4,6-dimethyl aniline (manufactured by Kanto Chemical Co., Inc.) (4.97g, 24.9mmol) and di-tert-butyl dicarbonate (manufactured by Kanto Chemical Co., Inc.) (13.6g, 62.1mmol) They were weighed, and dissolved by adding dehydrated toluene (manufactured by Kanto Chemical Co., Inc.) (35 mL). Introducing a reaction vessel in an oil bath preset at 90 ° C., and reacted for 33 hours. After completion of the reaction, the solvent was removed by silica column chromatography (hexane: ethyl acetate = 20: 1) as a white solid (2-bromo-4,6-dimethylphenyl) - carbamic acid tert-butyl ester was isolated ( 5.10g, 17.0mmol, 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 120℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With palladium diacetate; sodium carbonate; catacxium A In N,N-dimethyl acetamide at 120℃; for 16h; Inert atmosphere; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride In lithium hydroxide monohydrate at 25℃; for 0.333333h; Inert atmosphere; Stage #2: With NaNO2 In lithium hydroxide monohydrate at -5℃; for 1h; Inert atmosphere; Stage #3: bis(cyclopentadienyl) iron(II) With aminosulfonic acid; anhydrous Sodium acetate In dichloromethane; lithium hydroxide monohydrate at 25℃; for 12h; Inert atmosphere; Schlenk technique; | 2. Synthesis of 2-Bromoarylferrocene1-5 General procedure: Step 1: 2-Bromoaniline (1.03 g, 6 mmol; 1 equiv.) was dissolved in 25 mL distilled water at room temperature and 12 M hydrogen chloride (8 mL, 96 mmol; 16 equiv.) was dropwise over 20 minutes to the mixture. The resulting reaction mixture was cooled down to -5 °C using an ice bath. Sodium nitrite (0.49 g, 7.2 mmol; 1.2 equiv.) was dissolved in 1.5 mL water and cooled down to -5 °C, which was added dropwise to the main reaction mixture. The resulting mixture was stirred for 1.0 hours at -5°C. Finally, sulfamic acid (0.69 g, 7.2 mmol; 1.2 equiv.) and dichloromethane (30 mL) were added to the reaction mixture sequentially at room temperature. Step 2: To another dried 250 mL Schlenk flask equipped with a stirring bar was charged with ferrocene (1.12 g, 6 mmol; 1 equiv.) and sodium acetate (0.98 g, 7.2 mmol; 1.2 equiv.). This flask was closed with a plug, evacuated, back-filled with nitrogen. Next, The reaction mixture of Step 1 was added to the mixture of ferrocene and sodium acetate. The resulting mixture was stirred at room temperature overnight. The reaction was extracted with dichloromethane. The combined organic phase was washed with brine, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the crude product was obtained purified by column chromatography (PE) to give the 2-bromophenylferrocene 1a as orange solid. |
Stage #1: 2-bromo-4,6-dimethylaniline With hydrogenchloride; lithium hydroxide monohydrate; NaNO2 at -5 - 20℃; for 1h; Inert atmosphere; Stage #2: bis(cyclopentadienyl) iron(II) With aminosulfonic acid; anhydrous Sodium acetate In dichloromethane at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / toluene / 16 h / Reflux; Inert atmosphere 2: potassium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / toluene; N,N-dimethyl acetamide / 6 h / Reflux; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate / toluene / 12 h / 100 °C / Inert atmosphere 2: tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide; toluene / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100℃; for 12h; Inert atmosphere; | |
63% | With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene for 16h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; hydrogen bromide In water; 1,2-dichloro-ethane at 120℃; for 12h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 48h; Inert atmosphere; Reflux; | 23.1 Step 1: Synthesis of 3,5-dimethyl-6-phenanthridinamine Step 1: Synthesis of 3,5-dimethyl-6-phenanthridinamine Added together 2-cyanophenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) to a 125 mL of a 95/5 mixture of toluene/methanol. The solvents were degassed and the reaction mixture heated to reflux for 48 hours. After cooling, the reaction mixture was vacuum filtered and the organics evaporated and crude product was purified using silica gel column chromatography treated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants. The pure product was collected and concentrated to give 3,5-dimethyl-6-phenanthridinamine (9.1 g, 82% Yield). |
82% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 48h; Reflux; | 23.1 Production of es14 Step 1: synthesis of 3,5-dimethyl-6-phenanthridinamine 2-cyano-phenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis palladium(0)(triphenylphosphine) ( 2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) was added with the mixture of the 125 95/5 toluene / methanol. It was degassed and the solvent, heating under reflux for 48 hours the reaction mixture. After cooling, the reaction mixture was vacuum filtered, and evaporated organic material, the crude product and triethylamine as an eluent, 1: 9 ethyl acetate and was purified using chromatography on a column of silica gel treated with a mixture of methylene chloride. Collecting the pure product and concentrated to give the 3,5-dimethyl-6-phenanthridin-amine (9.1 g, 82% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium phosphate; 2C32H41O4P*Pd(2+)*2Cl(1-) In toluene at 110℃; for 16h; Inert atmosphere; | 4.9 General procedure for Suzuki-Miyaura coupling run in organic solvent General procedure: A dried and argonated Schlenk tube containing a magnetic stir bar was charged with aryl halide (1mmol), arylboronic acid (1.5mmol), 3mL of appropriate solvent, base (3mmol), and catalyst (see Table 1). The flask was evacuated, backfilled with argon and placed in to the oil bath (kept at appropriate temperature) on a magnetic stirrer for 16h. After that 20mL of water was added to the reaction mixture and product was extracted with methylene chloride (3×10mL), combined organic layer was dried over MgSO4, filtered, solvent was evaporated and the product was isolated by column chromatography. Yields: 64-99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With 2C32H41O4P*Pd(2+)*2Cl(1-); water In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; | 4.11 General procedure for Suzuki-Miyaura run in water General procedure: Preparation of catalyst: 10mL flask was charged with a stirrer, Pd(OAc)2 (0.02mmol, 2mol%), ligand (Sym-Phos, PPh3, PhPCy2, S-Phos) (0.04mmol, 4mol%) and 1mL of THF. The flask was evacuated, backfilled with argon, and the reaction mixture was stirred for 10min at ambient temperature. Such prepared catalyst was used in the coupling reactions. Similarly were prepared catalysts based on PdCl2 complexes. Reaction setup. A round-bottom flask containing magnetic stir bar was charged with 15mL of 0.3% aqueous solution of SDS and base (3mmol). Then aryl halide (1mmol) dissolved in a minimum amount of THF, arylboronic acid or its derivative (1.5mmol) and the pre-catalyst (see above) were added. The flask was placed in to the oil bath (kept at 60°C) and reaction mixture was stirred for next 16h. The product was filtered or extracted with methylene chloride or (3×10mL), then combined organic layer was dried over MgSO4, filtered, solvent was evaporated and the product was isolated by column chromatography. Yields: 63-99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid In 1-methyl-pyrrolidin-2-one at 20 - 100℃; | 3.a a) Synthesis of A/-(2-bromo-4,6-dirnethyl-phenyl)-iH-benzimidazol-2-amine a) Synthesis of A/-(2-bromo-4,6-dirnethyl-phenyl)-iH-benzimidazol-2-amine 2-Chlorobenzimidazole (6.9 g, 45.4 mmol) and 2-bromo-4,6-dimethylaniline (10.0 g, 50.0 mmol) are dissolved in NMP (23 imL) at 20°C. Methanesulfonic acid (4.8 g, 50.0 mmol) is added dropwise over ca. 0.5 h. The resulting suspension is heated to 100°C and stirred until complete conversion of 2-chlorobenzimidazole. The reaction mixture is then cooled to 20°C, diluted with water (14 ml.) and neutralized with 30 w-% aqueous sodium hydroxide (12.7 g, 95.3 mmol). The precipitated reaction product is isolated by filtration, washed with water and dried under vacuum at 90°C. Crude A/-(2-bromo-4,6-dimethyl-phenyl)- iH- benzimidazol-2-amine (10.3 g, 72%) is obtained as an off-white amorphous solid, which was further purified by recrystallization from methanol. 1 H-NMR (DMSO-d6): δ = 2.21 (s, 3H), 2.31 (s, 3H), 6.83-6.95 (m, 2H), 7.06-7.18 (m, 3H), 7.39 (brs, 1 H), 8.58 (brs, 1 H), 10.75 (brs, 1 H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: 2-bromo-4,6-dimethylaniline With sulfuric acid In water Heating; Stage #2: With sodium nitrite In water at 0 - 5℃; for 1h; Stage #3: With sodium azide In water; Petroleum ether at 10 - 20℃; for 4h; | |
73% | With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; palladium diacetate; potassium iodide; tricyclohexylphosphine In 1-methyl-pyrrolidin-2-one at 130℃; for 72h; | Preparation of 1,3,6,8-tetramethylcarbazole (III) 1.36 mL (10.0 mmol) of 1-bromo-2,4-dimethylbenzene, 2.405 g (12.0 mmol) of 2-bromo-4,6-dimethylaniline, 0.115 g (0.05 mmol) of palladium diacetate, 1.61 mL (1.0 mmol) of tricyclohexylphosphine (1.0 mmol), 6.365 g (3.0 mmol) of K3PO4, and 0.5 g (0.30 mmol) of KI were added to a 200 mL 3-necked round bottom flask including 125 mL of N-methyl-2-pyrrolidone (NMP) as solvent. The flask was equipped with a condenser and stir bar, and the reaction was heated to 130° C. for 72 hours. Diethyl ether (200 mL) and DI water (200 mL) were added to the reaction after cooling to room temperature. The organic layer was washed with brine (100 mL), dried over MgSO4, filtered to remove the drying agent and any reduced palladium, and concentrated using rotary evaporation. The product was purified by column chromatography on silica using a dichloromethane/hexanes gradient. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); caesium carbonate In dimethyl sulfoxide at 90℃; for 12h; Schlenk technique; Autoclave; | |
51% | With palladium diacetate; caesium carbonate; catacxium A In 1,4-dioxane at 80℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: 2-bromo-4,6-dimethylaniline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | |
66% | With sodium hydride In N,N-dimethyl-formamide | Preparation of Substrates 4a-p and 4c-D General procedure: According to the procedure given for preparation of S1 from 2-iodoaniline (see above), thereaction of 2-bromo-4,6-dimethylaniline (Aldrich, 1.01 g, 5.05 mmol) with iodomethane (7.06 g,49.7 mmol) was carried out at room temperature using NaH (ca. 60% dispersion in mineral oil,1.00 g, 25.0 mmol) and DMF (20 mL). S9 (0.759 g, 3.33 mmol, 66% yield) was obtained as acolorless oil after purification by column chromatography on silica gel (eluent: hexane:Et2O =10:1) and Kugelrhor distillation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0 - 20℃; Schlenk technique; | General Procedure: General procedure: Phenylglyoxylic acid (0.0133 mol, 1.0 equiv.)was dissolved in dry CH2Cl2 (40 mL) and the mixture was cooled to0 °C. Oxalyl chloride (0.0159 mol, 1.2 equiv.) was added dropwiseto the mixture followed by addition of DMF (cat, few drops). Theresulting mixture was stirred at 0 °C for 30 min and then warmedto room temperature. The mixture was then stirred for additional 3 h in which time no more gasevolution was seen. The solvent was removed under reduced pressure to give the correspondingacid chloride. The residue was dissolved in dry CH2Cl2 (40 mL) and the mixture was cooled to 0 °C.The corresponding ortho-bromo-aniline (0.0159 mol, 1.2 equiv.) was added followed by dropwiseaddition of NEt3 (0.0266 mol, 2.0 equiv.). The resulting mixture was stirred at room temperatureovernight. HCl (1 M, aq) was added (40 mL) to quench the reaction. An extraction with CH2Cl2(3×30 mL) followed by washing of the organic phase with brine (40 mL) was the next step. Theorganic phases were dried over MgSO4, filtered and concentrated under reduced pressure toafford the crude product. Purification with silica gel chromatography using hexane/CH2Cl2 (1/1) aseluent afforded the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 90℃; for 16h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 2-bromo-4,6-dimethylaniline; tert-butyl benzoyl(tert-butoxycarbonyl)carbamate With cesium fluoride In acetonitrile at 100℃; for 10h; Sealed tube; Inert atmosphere; Stage #2: With 1,10-Phenanthroline; potassium carbonate; copper(l) chloride In acetonitrile at 90℃; for 10h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In dichloromethane at 20℃; for 1h; | 1 Step-1: Preparation of N-(2-bromo-4,6-dimethylphenyl)-2,2,2-trifluoroacetamide (189b) Compound 189b was prepared according to the procedure reported in step-1 of scheme-46, from 2-bromo-4,6-dimethylaniline (189a) (7 g, 35.0 mmol; CAS 41825-73-4) in DCM (30 mL) using triethylamine (6.02 g, 59.5 mmol), trifluoroacetic acid anhydride (11.02 g, 52.5 mmol) and stirring at RT for 1 h. This gave after workup N-(2-bromo-4,6-dimethylphenyl)- 2,2,2-trifluoroacetamide (189b) (10.32 g, 100% yield) as a pale-yellow solid;lH NMR (300 MHz, DMSOntife) δ 11.12 (s, 1H), 7.43 (s, 1H), 7.18 (s, 1H), 2.30 (s, 3H), 2.16 (s, 3H);19F NMR (282 MHz, DMSO-i/6) δ -74.08; MS (ES+): 296/298 (M+l); (ES-): 294/296 (M-l). |
88% | With dmap In 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In N,N-dimethyl acetamide at 150℃; for 0.0833333h; Microwave irradiation; | General procedure: In a 20mL microwave reaction vial (Biotage), a mixture of substituted 2-halogeno-aniline (1 equiv, 500 mg), O-isopropylxanthic acid potassium salt (PIX) (2 equiv), and DMAC (8 mL) was added. The vial was irradiated at 150 °C for 5 min in a Biotage microwave reactor. The mixture was cooled to room temperature. Then it was poured into cold H2O and adjusted to pH 3 by HCl 1N. The precipitate was filtered and washed (5 times) with H2O to afford products without additional purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 125℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With trifluoroacetic acid for 4h; Reflux; | Synthesis of compounds 8b-g (general procedure). General procedure: The starting aniline (50 mmol), triethyl orthoacetate (200 mmol), and a drop of tri uoroacetic acid were mixed in a 50-mL round-bottom ask. The reaction mixture was re uxed for 4 h and cooled to room temperature. Ethanol formed during the reaction was distilled off at atmospheric pressure, the residue was concen-trated in vacuo to obtain compounds 8b-g as colorless oils. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 36h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With toluene-4-sulfonic acid In chloroform; toluene at 120℃; for 96h; Inert atmosphere; Dean-Stark; | 4.2. Synthesis of 1a General procedure: In a round bottom flask, 2-(4-methylphenyl)malondialdehyde(0.500 g, 3.08 mmol) was dissolved in chloroform (10 mL). To thissolution, 2-bromo-3-methylaniline (1.175 g, 6.32 mmol) and ptoluenesulfonic acid (0.027 g, 0.15 mmol) in toluene (40 mL) were added. A dean-stark trap was used during the reflux. The reactionwas heated at 120 C and stirred for four days. It was then cooled toroom temperature and the solvents were removed using a rotaryevaporator. Methanol (15 mL) was added to the resulting oil to precipitatethe desired solids. The resulting solids were kept in methanolin a 35 C freezer overnight and then collected by suctionfiltration, washed with cold methanol (20 mL) and cold acetone(20 mL). The resulting yellow solids were dried under reducedpressure (1.172 g, 76.3% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: 2-bromo-4,6-dimethylaniline; trifluoroacetic acid In acetonitrile at 20℃; for 1h; Stage #2: 1,2-Dicyanoethylene With sodium decatungstate In water monomer; acetonitrile at 20℃; for 12h; UV-irradiation; |
Tags: 41825-73-4 synthesis path| 41825-73-4 SDS| 41825-73-4 COA| 41825-73-4 purity| 41825-73-4 application| 41825-73-4 NMR| 41825-73-4 COA| 41825-73-4 structure
[ 397323-70-5 ]
(2-Amino-3-bromophenyl)methanol
Similarity: 0.88
[ 397323-70-5 ]
(2-Amino-3-bromophenyl)methanol
Similarity: 0.88
[ 397323-70-5 ]
(2-Amino-3-bromophenyl)methanol
Similarity: 0.88
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