* 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.
3.3 Step 3) (2-Amino-5-methylphenyl)(phenyl)methanone
(0165) To a solution of N-(2-Benzoyl-4-methylphenyl)benzamide (1.32 g) in MeOH at room temperature was added NaOH (1.4 g) in water (2 mL) and heated to reflux overnight. The reaction solution was washed with water and extracted with ethyl acetate. The compound was obtained as a yellow oil.
Stage #1: <i>p</i>-toluidine; benzoyl chloride at 120 - 140℃; for 2h;
Stage #2: With zinc(II) chloride at 160℃; for 3h;
Stage #3: With sulfuric acid at 140℃; for 2h;
Preparation of 2-amino-5-methylbenzophenone (IV)
Benzoyl chloride (133.6 mL, 1.15 mol) was placed in a reaction flask, stirred, heated to 120 ° C,Add p-toluidine slowly (50 · 00g, 0.46mol), add the temperature to 140 ° C,After 2 hours, anhydrous ZnC12 (79.06g, 0.58mol) was added and the temperature was raised to 160 ° C for 3 hours. After cooling to 100 ° C, 200 mL of water was added and the mixture was cooled and cooled. To the residue in the reaction flask was added 70% sulfuric acid (150 mL), stirred at 140 ° C for 2 hours. After cooling, the reaction solution was poured into a large amount of water, extracted with aqueous ammonia and extracted with ethyl acetate. The ethyl acetate , And the solid was recrystallized from 95% ethanol to give a yellow solid(79.70 g, yield 82.2%).
at 220 - 230℃; man kocht das Reaktionsprodukt mit alkoh. Salzsaeure;
With zinc(II) chloride at 220℃; Erwaermen des Reaktionsprodukts mit wss.-aethanol. Salzsaeure;
Stage #1: <i>p</i>-toluidine; benzoyl chloride With zinc(II) chloride at 205℃; for 2h;
Stage #2: With sulfuric acid for 8h; Heating;
Stage #1: 2-amino-5-methylbenzophenone With sulfuric acid; acetic acid; sodium nitrite In water at 0℃; for 1h;
Stage #2: With copper In water at 80℃; for 2h;
Preparation of 2-methylfluorenone (V)
120 mL of water, 120 mL of acetic acid and 37.8 g of sulfuric acid were placed in a reaction flask, and 2-amino-5-methylbenzophenone (40.0g) was added and stirred to dissolve clear,Followed by cooling to 0 °, dropping 25 mL of aqueous sodium nitrite (13.258, 0.19 mil)After 1 hour of dropping, 4 g of copper powder was added and the temperature was raised to 80 ° C for 2 hours.Cooled to room temperature, extracted with dichloromethane, and the solvent was removed by rotary distillation. The solid was recrystallized from 90% ethanol to give a yellow solid (30.04 g, 82.4%).
With hydrogenchloride In ethanol for 2h; Heating; Yield given;
Stage #1: N-(2-benzoyl-4-methylphenyl)acetamide With hydrogenchloride In methanol; water for 2h; Reflux;
Stage #2: With sodium hydroxide In water
Representative procedure for synthesis of substituted 2-aminobenzophenones
General procedure: The 2-acetamidobenzophenone obtained as described above was heated under reflux with 100 mL MeOH-HCl (MeOH:6 mol/L HCl = 1:1) in a round-bottomed flaskfor 2 h. The hot mixture was poured into a beaker and cooled. The hydrochloride ofthe 2-aminobenzophenone was isolated by suction filtration, washed with chilled alcohol, then suspended in 800 mL water in a beaker with a mechanical stirrer. The pH was adjusted to 8.0 by addition of a solution of 2 mol/L sodium hydroxide. The mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over MgSO4, and concentrated. The crude product was purified by recrystallization or by column chromatography on silica gel with petroleum ether-ethyl acetate as eluent.
In N,N-dimethyl-formamide at 160℃; for 0.5h; Molecular sieve; Microwave irradiation;
1.2 [00168] 3-acetyl-6-methyl-4-phenyl-1,2-dihydroquinolin-2-one (EV-AS5446-002) - Step 2
[00169] To a solution of 2-benzoyl-4-methylaniline (EV-AS5441-001, 250 mg, 1.12 mmol) in DMF (2 ml) was added ethyl 3-oxobutanoate (213 _, 1.69 mmol) and 4A molecular sieves (60 mg) and the mixture was stirred and heated at 160C for 30min under microwave irradiation. The reaction mixture was concentrated in vacuo to afford a beige powder. Trituration using EtOAc, and washing with Et20 afforded 311mg (66%) of 3-acetyl-6-methyl-4-phenyl-1,2-dihydroquinolin-2-one (EV-AS5446-002) as a pale yellow powder. LCMS (method D): retention time l . lOmin, M/z = 277.9 (M + 1).
61%
With cerium(III) chloride heptahydrate In neat (no solvent) for 0.133333h; Microwave irradiation;
6-methyl-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,2-dihydroquinolin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 2 steps
1: 82 percent / 160 °C
2: 50 percent / aq. NaOH / aq. ethanol / 15 - 30 °C
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide / 0.5 h / 160 °C / Molecular sieve; Microwave irradiation
2.1: potassium hydroxide; water / ethanol / 0.33 h / 0 °C
2.2: 2 h / 0 - 20 °C
With stannous chloride In hydrogenchloride; water; ethyl acetate
12.A A.
A. 5-Methyl-3-phenyl-1H-indazole To a solution of 2-amino-5-methylphenyl phenyl ketone (2.0 g, 9.5 mmol) in HCl (45 mL of a 6M solution) at 0° C. was added sodium nitrite (NaNO2) (719 mg, 10.4 mmol) in water (2 mL). The reaction was stirred for 30 min when the homogeneous solution was added dropwise to a solution of SnCl2 (5.88, 26 mmol) in concentrated HCl (15 mL) at room temperature. The reaction was stirred for 30 min when it was filtered. The solid was then taken up in ethyl acetate (80 mL) and saturated sodium bicarbonate (80 mL). The suspension was then filtered and the ethyl acetate layer dried (Na2SO4) and concentrated to give the product (1.59 g, 80% yield). (1H NMR (DMSO-d6) δ 7.96 (d, 2H), 7.85 (br s, 1H), 7.54-7.46 (m, 3H), 7.39 (t, 1H), 7.24 (d, 1H), 2.45 (s, 3H); ES-MS (m/z) 209 [M+1]+.
80%
With stannous chloride In hydrogenchloride; water; ethyl acetate
12.A A.
A. 5-Methyl-3-phenyl-1H-indazole To a solution of 2-amino-5-methylphenyl phenyl ketone (2.0 g, 9.5 mmol) in HCl (45 mL of a 6M solution) at 0° C. was added sodium nitrite (NaNO2) (719 mg, 10.4 mmol) in water (2 mL). The reaction was stirred for 30 min when the homogeneous solution was added dropwise to a solution of SnCl2 (5.88, 26 mmol) in concentrated HCl (15 mL) at room temperature. The reaction was stirred for 30 min when it was filtered. The solid was then taken up in ethyl acetate (80 mL) and saturated sodium bicarbonate (80 mL). The suspension was then filtered and the ethyl acetate layer dried (Na2SO4) and concentrated to give the product (1.59 g, 80% yield). (1H NMR (DMSO-d6) δ 7.96 (d, 2H), 7.85 (br s, 1H), 7.54-7.46 (m, 3H), 7.39 (t, 1H), 7.24 (d, 1H), 2.45 (s, 3H); ES-MS (m/z) 209 [M+1]+.
2-(1-methoxyethylideneamino)-5-methylbenzophenone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
6 EXAMPLE 6
EXAMPLE 6 A procedure mentioned below is conducted in the same manner as example 1. 2-Amino-5-methylbenzophenone is reacted with methyl orthoacetate, whereby 2-(1-methoxyethylideneamino)-5-methylbenzophenone is obtained.
With potassium carbonate In xylene under Ar; mixt. of iodo-ferrocene, amine, Cu powder, and K2CO3 in xylenestirred at 140°C for 6 h; extn. with ethyl acetate, org. phases washed with water and brine, driedover MgSO4, filtrate evapd., column chromy. (petroleum/ethyl acetate); elem. anal.;
With cesium fluoride In acetonitrile at 20℃; Inert atmosphere; Overall yield = 57 %;
General procedure for the preparation of oxadisilole fused acridines5aei, dioxatrisilole-fused acridines 6 a-i or benzo[b]acridinederivatives 10 a-g.
General procedure: TfOH (0.14 mL, 1.50 mmol) was added by meansof a syringe to a stirred solution of PhI(OAc)2, (247 mg, 0.75 mmol)in CH2Cl2 (10 mL) at 0°C under N2. The mixture was stirred under N2 at 0°C for 1 h and at room temperature for 2 h. The clearyellow solution was cooled again to 0°C , followed by dropwiseaddition into the cold solution of the benzobis(oxadisilole) 1 (or 2,3-naphthoxadisilole 7) (0.5 mmol) in CH2Cl2 (5 mL) at 0°C . Themixture was stirred at 0°C for 0.5 h and at room temperature for 3 h. The clear yellow solution was washed with water (200 mL)and was extracted by CH2Cl2 three times. Then the low yellowsolid was obtained under reduced pressure and resolved in CH3CN(5 mL). The solution of 2-aminoaryl ketones or 2-aminoaryl aldehydes 4a-i (0.2 mmol) and CsF (76 mg, 0.5 mmol) in CH3CN (5 mL) was dropwise added into low yellow solution of 2 (or 8),The mixture stirred under N2 at room temperature until 4a-i wasdisappeared (monitored by TLC). The crude product was purifiedby column chromatography on silica gel using a gradient of 4-5%EtOAc in PE (60-80 C) as the eluent to afford products 5a-i, 6a-i and 10a-g.
With cesium fluoride In acetonitrile at 20℃; Inert atmosphere;
General procedure for the preparation of oxadisilole fused acridines5aei, dioxatrisilole-fused acridines 6 a-i or benzo[b]acridinederivatives 10 a-g.
General procedure: TfOH (0.14 mL, 1.50 mmol) was added by meansof a syringe to a stirred solution of PhI(OAc)2, (247 mg, 0.75 mmol)in CH2Cl2 (10 mL) at 0°C under N2. The mixture was stirred under N2 at 0°C for 1 h and at room temperature for 2 h. The clearyellow solution was cooled again to 0°C , followed by dropwiseaddition into the cold solution of the benzobis(oxadisilole) 1 (or 2,3-naphthoxadisilole 7) (0.5 mmol) in CH2Cl2 (5 mL) at 0°C . Themixture was stirred at 0°C for 0.5 h and at room temperature for 3 h. The clear yellow solution was washed with water (200 mL)and was extracted by CH2Cl2 three times. Then the low yellowsolid was obtained under reduced pressure and resolved in CH3CN(5 mL). The solution of 2-aminoaryl ketones or 2-aminoaryl aldehydes 4a-i (0.2 mmol) and CsF (76 mg, 0.5 mmol) in CH3CN (5 mL) was dropwise added into low yellow solution of 2 (or 8),The mixture stirred under N2 at room temperature until 4a-i wasdisappeared (monitored by TLC). The crude product was purifiedby column chromatography on silica gel using a gradient of 4-5%EtOAc in PE (60-80 C) as the eluent to afford products 5a-i, 6a-i and 10a-g.
With tert.-butylhydroperoxide; copper(II) choride dihydrate; ammonium acetate In water at 80℃;
2.2. Experimental Procedure for preparation of 3
General procedure: Substrate 1 (0.2 mmol), NH4OAc (31.2 mg, 0.4 mmol),CuCl2*2H2O (6.8 mg, 20 mol%), TBHP (90 mL, 70% aq, 0.6 mmol),were added to a tube, followed by addition of solvent 2 (2 mL). The mixture was stirred at assigned temperature and monitored by TLC. The solution was cooled to r.t., diluted with ethyl acetate(5 mL), washed with saturated aqueous sodium hydrogen sulfite.The aqueous layers was extracted with EtOAc (3 10 mL), the combined organic layers were dried over Na2SO4, filtered, and evaporated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate= 20:1) to afford the desired product 3.
With oxygen; caesium carbonate In dimethyl sulfoxide at 140℃; for 8h;
2. Typical procedure for the synthesis of 2a
General procedure: A solution of 2-phenylindole (1a, 97 mg, 0.5 mmol) and Cs2CO3 (326 mg, 1.0 mmol) in DMSO (1.5 mL) was heated to 140 °C for 8 h under O2 balloon atmosphere. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 10:1), 2-aminobenzophenone (2a) was obtained as a yellow solid, 59 mg (60 %). Other compounds were prepared similarly, and the spectroscopic data of compounds 2a-l, 4 and 5 are as follows.
Stage #1: 3-bromopropyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 70℃; for 12h; Inert atmosphere;
Stage #2: 2-amino-5-methylbenzophenone In tetrahydrofuran at 70℃; for 12h;
With water; In tetrahydrofuran; diethyl ether; at 20℃; for 17.5h;Cooling with ice;
[00341] To a solution of 3M bromo(phenyl)magnesium in Et20 (22.7 ml) was added a solution of <strong>[5925-93-9]2-amino-5-methylbenzonitrile</strong> (CAS 5925-93-9, 3 g, 22.7 mmol) in anhydrous THF (30 ml) over 0.5h. The ice bath was removed and the reaction stirred at room temperature for 17h. The solution was cooled in an ice bath and 1M aq HCl (90 ml) was added. The mixture was extracted with Et20 (4 x 100 ml) and the organic extracts were washed with 1M aq HCl (40 ml), water (2 x 30 ml), saturated NaHC03 (40 ml) and brine (40 ml) then dried over MgS04 and concentrated in vacuo to obtain 5008 mg (quant) of 2-benzoyl-4-methylaniline (EV-AQ3873-001) as a brown solid. LCMS data not recorded.
ethyl 2-[(2-benzoyl-4-methylphenyl)carbamoyl]acetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
31.2 [00342] ethyl 2-[(2-benzoyl-4-methylphenyl)carbamoyl]acetate (EV-AQ3875-001) - Step 2
[00343] ethyl 3-chloro-3-oxopropanoate (1.45 ml, 11.36 mmol) was added dropwise to a cold (0C) solution of 2-benzoyl-4-methylaniline (EV-AQ3873-001, 2 g, 9.47 mmol) and DIPEA (1620.6 _, 9.47 mmol) in DCM (15 ml) under a nitrogen atmosphere. The resulting solution was stirred and allowed to warm to room temperature over 1H. The mixture was diluted with water and extracted with DCM. The organics were dried over MgS04 to obtain 3.5 g (quant) of ethyl 2-[(2- benzoyl-4-methylphenyl)carbamoyl]acetate (EV-AQ3875-001) as a dark oil. LCMS (method D): retention time 1.20min, M/z = 326 (M + 1).
3,6'-dimethyl-3-methyl-1,4'-diphenylspiro[pyrazole-4,2'(1'H)-quinazolin]-5(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With ammonium acetate In ethanol for 1h; Reflux;
General procedure for the preparation of spiro compounds 5a-h, 6a-h, and 7a-h from 1-3, 4a-h,and ammonium acetate.
General procedure: A mixture of 1-3 (1.0 mmol), 4a-h (1.0 mmol), and ammonium acetate (0.308g, 4.0 mmol) in EtOH (10 mL) was refluxed for 1 h. After removal of the solvent in vacuo, cold H2O wasadded to the residue. The resulting mixture was extracted with CHCl3 (60 mL). The extract was driedover anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatographyon silica gel with CHCl3 as the eluent to give 5a-h, 6a-h, and 7a-h.
3,6'-dimethyl-1-(4-methylphenyl)-4'-phenylspiro[pyrazole-4,2'(1'H)-quinazolin]-5(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With ammonium acetate In ethanol for 1h; Reflux;
General procedure for the preparation of spiro compounds 5a-h, 6a-h, and 7a-h from 1-3, 4a-h,and ammonium acetate.
General procedure: A mixture of 1-3 (1.0 mmol), 4a-h (1.0 mmol), and ammonium acetate (0.308g, 4.0 mmol) in EtOH (10 mL) was refluxed for 1 h. After removal of the solvent in vacuo, cold H2O wasadded to the residue. The resulting mixture was extracted with CHCl3 (60 mL). The extract was driedover anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatographyon silica gel with CHCl3 as the eluent to give 5a-h, 6a-h, and 7a-h.
1-(4-chlorophenyl)-3,6'-dimethyl-4'-phenylspiro[pyrazole-4,2'(1'H)-quinazolin]-5(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
72%
With ammonium acetate In ethanol for 1h; Reflux;
General procedure for the preparation of spiro compounds 5a-h, 6a-h, and 7a-h from 1-3, 4a-h,and ammonium acetate.
General procedure: A mixture of 1-3 (1.0 mmol), 4a-h (1.0 mmol), and ammonium acetate (0.308g, 4.0 mmol) in EtOH (10 mL) was refluxed for 1 h. After removal of the solvent in vacuo, cold H2O wasadded to the residue. The resulting mixture was extracted with CHCl3 (60 mL). The extract was driedover anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatographyon silica gel with CHCl3 as the eluent to give 5a-h, 6a-h, and 7a-h.
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
With n-butyllithium In tetrahydrofuran at -78℃;
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2-amino-N-methoxy-N,5-dimethylbenzamide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Multi-step reaction with 2 steps
1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
1.2: Inert atmosphere; Reflux
2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere
Multi-step reaction with 2 steps
1: 1,1'-carbonyldiimidazole; triethylamine / tetrahydrofuran / Reflux
2: n-butyllithium / tetrahydrofuran / -78 °C
Multi-step reaction with 3 steps
1: sodium carbonate / tetrahydrofuran / 0 - 20 °C
2: dichloromethane / 2 h / -78 °C
3: sodium hydroxide; water / methanol / Reflux
Multi-step reaction with 2 steps
1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.5 h / 65 °C
1.2: 3 h / 80 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
Multi-step reaction with 2 steps
1.1: tetrahydrofuran / 2 h / 65 °C
1.2: Reflux
2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
(9S,9aS)-9a-hydroxy-7-methyl-9-phenyl-9-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)-1,2,9,9a-tetrahydro-3H-pyrrolo[1,2-a]indol-3-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 4 steps
1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: acetic acid / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere; Sealed tube
3.1: acetic anhydride; triethylamine / 80 °C / Inert atmosphere
4.1: (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium t-butanolate / tert-butyl methyl ether / 0.08 h / Inert atmosphere; Sealed tube
4.2: 4 h / 20 °C / Inert atmosphere; Sealed tube
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2-amino-5-methylbenzophenone In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: 2-amino-5-methylbenzophenone In tetrahydrofuran at 50℃; for 5h; Inert atmosphere;
Substrates 2~14 were synthesized according to Method A[2].Method A:
General procedure: To a stirred solution of Ph3PCH2(R)Br (1.5 equiv, 7.5 mmol) in dry THF (10 mL) was added t-BuOK (1.5 equiv, 7.5 mmol) in portions under nitrogen. After the mixture was stirred at room temperature for 0.5 h, then added the benzophenone (1 equiv, 5 mmol) in it. The reaction mixture was then stirred at 50°C for 5 h under nitrogen. The reaction mixture was quenched with water and extracted with DCM (2 x 30 mL). The combined organic layers were dried over anhydrous Na2SO4, and concentrated on rotary evaporator under vacuum and the residue was purified by column chromatography on silica gel.
6-methyl-4-phenyl-2-(quinolin-2-yl)quinazoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With ammonium acetate; oxygen; trifluoroacetic acid; copper dichloride In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique;
4.2. General procedure towards quinazolines 3
General procedure: 2-aminophenyl ketones 1 (0.3 mmol), methylazaarenes 2 (0.6 mmol), NH4OAc (0.6 mmol), CuCl2 (20 mol %), TFA (50 mol %), DMF (2.0 mL) were added to a 25mL Schlenk tube under O2 atmosphere with magnetic stirrer bar. The reaction mixture was stirred at 120 _C (oil bath temperature) for 24 h. After the reaction was finished (monitored by TLC), the mixture was cooled to room temperature, quenched with solution of NaHCO3 (10 mL) and extracted with EtOAc (3 _ 10 mL). The combined organic layers were dried over anhydrous MgSO4 and the solvent was removed under vacuum. The crude product was purified by column chromatography (EtOAc/hexanes) on silica gel.
With 3-chloro-benzenecarboperoxoic acid In toluene at 0 - 120℃; for 6h;
3.4 Step 4) (5-Methyl-2-nitrophenyl) (phenyl)methanone
(0166) To a solution of (2-Amino-5-methylphenyl) (phenyl)methanone (5.28 g) in toluene (200 mL) at 0°C. was added m-chloroperoxybenzoic acid (5 eq). The resulting mixture was heated to 120°C. and allowed to stir for 6 hours. After the completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase is concentrated under reduced pressure and separated by column chromatography. The compound was obtained as a pale-yellow oil.
(5-methyl-2-(p-tolylamino)phenyl)(phenyl)methanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With copper; potassium carbonate In chlorobenzene for 24h; Reflux;
4.1.1. General procedure for aryl amination
General procedure: To a round-bottom flask equipped with a reflux condenser and a magnetic bar were added Aminoacetophenone (5 mmol, 1 eq.), the corresponding halide (7.5 mmol, 1.5 eq.), K2CO3 (6.25 mmol, 1.25 eq.), and Cu (15 mol%) were suspended in PhCl (8 mL) and heated to reflux for 24 h and then cooled to room temperature. Water (15 mL) was added and the reaction was extracted with EtOAc (15 mL x 3). The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified via flash chromatography (0-5% EtOAc/hexanes). 1a-1m were prepared using known literture protocol and in agreement with the reported data [14a].
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