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CAS No. : | 360-03-2 | MDL No. : | MFCD00498146 |
Formula : | C8H6F2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PFKSLFZFBCIJOI-UHFFFAOYSA-N |
M.W : | 172.13 | Pubchem ID : | 726153 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-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 thionyl chloride | ||
With thionyl chloride In dichloromethane at 0 - 20℃; for 1.5h; Schlenk technique; | ||
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; | 33.A To a solution of difluoro(phenyl)acetic acid (Ηagele, G., Haas, A. J. of FluorineChemistry (1996) 76, 15-19) (1.7 g, 10.4 mmol) in methylene chloride (25 mL) was added oxalylchloride (5.2 mL, 2M in methylene chloride, 10.4 mmol) and a drop of DMF at room temperature. After 1 hour, the reaction mixture was added to a suspension of trans-4-azido-3 -fluoropiperidine (1.5 g, 10 mmol) and resin-DEPEA (40 mmol eq) in methylene chloride (50 mL) at room temperature. After 2 hour, the reaction mixture was filtered and concentrated to yield the title compound (2.5 g) as a solid. MS: 299 (M+H1"). |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; | ||
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; | Acyl chlorides General procedure: The acid (5 mmol) was dissolved in anhydrous CH2Cl2 (10 mL) and DMF (a few drops) added.Oxalyl chloride (6 mmol, 1.2 equiv.) was added dropwise to the solution, that was cooled in an icewater bath. The resulting mixture was allowed to stir at room temperature for an additional 4 h andthe solvent was evaporated to afford the crude acyl chloride, which was used directly in the nextstep. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium hydroxide at 25℃; | |
With water; potassium carbonate In methanol at 25℃; for 2h; Inert atmosphere; | ||
With water; potassium carbonate In methanol at 20℃; for 3h; |
With sodium hydroxide In ethanol at 20℃; for 12h; | ||
at 20℃; Alkaline conditions; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With dmap; dicyclohexyl-carbodiimide In benzene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine; In dichloromethane; | 2. 1-(tert-Butoxycarbonyl)-4-(2,2-difluoro-2-phenylacetamido)-piperazine 2,2-Difluoro-2-phenylacetic acid (0.600 g, 0.0035 mol). N-(tert-butoxycarbonyl)piperazine (0.714 g, 0.0038 mol) and triethylamine (0.53 ml, 0.0038 mol) were added sequentially to 20 ml anhydrous dichloromethane under N2 at 25 C. <strong>[68641-49-6]Bis(2-oxo-3-oxazolidinyl)phosphinic chloride</strong> (0.967 g, 0.0038 mol) was added and the reaction stirred for 2 h. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with H2 O (20 ml), brine, dried over MgSO4 and evaporated. The residue was chromatographed on silica eluding with 20-40% ethyl acetate-hexane to yield the title compound as a colourless oil (1.0 g, 84%). delta(250 MHz, CDCl3) 1.44 (9H, s), 3.21 (2H, m), 3.24 (4H, m), 3.44 (2H, m), 7.45-7.62 (5H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
125 EXAMPLE 125 EXAMPLE 125 N-{3-[1-(3-[DIFLUORO(PHENYL)ACETYL]AMINO}PROPYL)-4-PIPERIDINYL]PHENYL}-2-METHYLPROPANAMIDE: Example 125 was prepared from 2,2-difluoro-2-phenylacetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.71 (s, 1H), 7.65-7.62 (m, 2H), 7.50 (s, 1H), 7.47-7.40 (m, 3H), 7.35 (d, 1H, J=7.6 Hz), 7.22 (t, 1H, J=7.2 Hz), 6.95 (d, 1H, J=7.8 Hz), 3.45 (q, 2H, J=5.3 Hz), 3.10(d, 2H, J=10.9 Hz), 2.59-2.45 (m, 4H), 2.11-2.02 (m, 2H), 1.89-1.71 (m, 6H), 1.20 (d, 6H, J=6.9 Hz); ESMS m/e: 458.4 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
124 EXAMPLE 124 EXAMPLE 124 N-{3-[1-(3-[DIFLUORO(PHENYL)ACETYL]AMINO}PROPYL)-4-PIPERIDINYL]-4-METHYLPHENYL}-2-METHYLPROPANAMIDE: Example 124 was prepared from 2,2-difluoro-2-phenylacetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 8.00 (s, 2H), 7.68-7.63 (m, 3H), 7.49-7.39 (m, 3H), 7.23 (d, 1H, J=1.8 Hz), 7.07 (d, 1H, J=8.3 Hz), 3.45 (q, 2H, J=4.9 Hz), 3.11 (d, 2H, J=10.2 Hz), 2.76-2.66 (m, 1H), 2.56 (t, 2H, J=5.0 Hz), 2.44 (septet, 1H, J=6.9 Hz), 2.28 (s, 3H), 2.13-2.05 (m, 2H), 1.82-1.71 (m, 6H), 1.15 (d, 6H, J=6.9 Hz); ESMS m/e: 472.4 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
136 EXAMPLE 136 EXAMPLE 136 N-{3-[1-(3-[DIFLUORO(PHENYL)ACETYL]AMINO}PROPYL)-4-PIPERIDINYL]-4-FLUOROPHENYL}-2-METHYLPROPANAMIDE: Example 136 was prepared from 2,2-difluoro-2-phenylacetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 9.11 (s, 1H), 7.61-7.56 (m, 2H), 7.41-7.34 (m, 4H), 7.21-7.17 (m, 1H), 7.14 (s, 1H), 6.88 (t, 1H, J=9.5 Hz), 3.39 (q, 2H, J=5.7 Hz), 3.08-3.01 (m, 2H), 2.84-2.74 (m, 1H), 2.50 (t, 2H, J=5.1 Hz), 2.38 (septet, 1H, J=7.2 Hz), 2.08-1.99 (m, 2H), 1.81-1.73 (m, 4H), 1.72 -1.64 (m, 2H), 1.17 (d, 6H, J=7.2 Hz); ESMS m/e: 476.2 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 0℃; Electrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: phenylacetyl chloride With pyridine; tin(II) trifluoromethanesulfonate; Selectfluor; potassium tetrakis(pentafluorophenyl)borate In acetonitrile at 20℃; for 3h; Inert atmosphere; Stage #2: With water In acetonitrile at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium fluoride / dimethyl sulfoxide / 15 h / 60 °C / Inert atmosphere 2: water; potassium carbonate / methanol / 2 h / 25 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: copper / dimethyl sulfoxide / 12 h / 60 °C / Inert atmosphere 2: potassium carbonate; water / methanol / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: copper / dimethyl sulfoxide / 12 h / 60 °C 2.1: potassium carbonate / water; methanol / 2 h / 20 °C 2.2: pH 1 |
Multi-step reaction with 2 steps 1: copper / dimethyl sulfoxide / 12 h / 60 °C / Inert atmosphere 2: sodium hydroxide / ethanol / 12 h / 20 °C | ||
Multi-step reaction with 2 steps 1: copper / dimethyl sulfoxide / 55 °C / Inert atmosphere 2: 20 °C / Alkaline conditions; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | at 70℃; for 16h; | 2. General Procedure A General procedure: In a screw-cap vial, the diamine or aminothiophenol (1 mmol) was dissolved in fluorinated carboxylic acid (2 mL, 0.5 M) and the reaction was stirred at 70 °C for 16 hours. The fluorinated carboxylic acid was then evaporated under reduced pressure and the crude product was purified by silica gel column chromatography to yield the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C / Schlenk technique 2: pyridine / dichloromethane / 0 °C / Schlenk technique 3: dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere 4: ammonium formate / 16 h / 20 - 80 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C / Schlenk technique 2: pyridine / dichloromethane / 0 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C / Schlenk technique 2: pyridine / dichloromethane / 0 °C / Schlenk technique 3: dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C60H54Cl2N3O6Pol With piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2,2-Difluoro-2-phenylacetic acid With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 1h; Inert atmosphere; | 2 Resin 33 (0.075 mmol, 190 mg) was suspended in DMF (2 mL x 5 min) and mixed with a stream of 2 every 30 seconds. The Fmoc group was removed from the resin-supported building block by mixing the resin twice with a solution of 2% DBU, 2% piperidine in DMF (2 mL x 5 min) while agitating with a stream of 2 every 30 seconds. The resin was washed six times with DMF (2 mL x 30 sec). α,α-Difluorophenylacetic acid (34; 0.1 M solution in DMF, 2.5 mL, 3.3 equiv, 0.25 mmol), followed by HATU (0.2M solution in DMF, 1.15 mL, 3.1 equiv, 0.23 mmol) and N-methyl morpholine (1.0 M in DMF, 0.5 mL, 6.7 equiv, 0.5 mmol) were added to the resin. The reaction mixture was agitated by a stream of nitrogen for 30 min. The reagents were drained from the reaction vessel, and the resin was washed six times with DMF (2 mL x 30 sec). α,α-Difluorophenylacetic acid (0.1 M solution in DMF, 2.5 mL, 3.3 equiv, 0.25 mmol), followed by HATU (0.2M solution in DMF, 1.15 mL, 3.1 equiv, 0.23 mmol) and N-methyl morpholine (1.0 M in DMF, 0.5 mL, 6.7 equiv, 0.5 mmol) were added to the resin. The reaction mixture was agitated by a stream of nitrogen for 30 min. The reagents were drained from the reaction vessel, and the resin was washed with six times DMF (2 mL x 30 sec), and six times with DCM (2 mL x 30 sec) to produce resin 35 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C65H61Cl2N4O7Pol With piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2,2-Difluoro-2-phenylacetic acid With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 1h; Inert atmosphere; | 3 Resin 42 (0.075 mmol, 105 mg) was suspended in DMF (2 mL x 5 min) and mixed with a stream of 2 every 30 seconds. The Fmoc group was removed from the resin-supported building block by mixing the resin twice with a solution of 2% DBU, 2% piperidine in DMF (2 mL x 5 min) while agitating with a stream of 2 every 30 seconds. The resin was washed six times with DMF (2 mL x 30 sec). α,α-Difluorophenylacetic acid (34; 0.1 M solution in DMF, 2.5 mL, 3.3 equiv, 0.25 mmol), followed by HATU (0.2M solution in DMF, 1.15 mL, 3.1 equiv, 0.23 mmol) and N-methyl morpholine (1.0 M in DMF, 0.5 mL, 6.7 equiv, 0.5 mmol) were added to the resin. The reaction mixture was agitated by a stream of nitrogen for 30 min. The reagents were drained from the reaction vessel, and the resin was washed six times with DMF (2 mL x 30 sec). α,α-Difluorophenylacetic acid (0.1 M solution in DMF, 2.5 mL, 3.3 equiv, 0.25 mmol), followed by HATU (0.2M solution in DMF, 1.15 mL, 3.1 equiv, 0.23 mmol) and N-methyl morpholine (1.0 M in DMF, 0.5 mL, 6.7 equiv, 0.5 mmol) were added to the resin. The reaction mixture was agitated by a stream of nitrogen for 30 min. The reagents were drained from the reaction vessel, and the resin was washed with six times DMF (2 mL x to produce resin 43. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C63H64ClN4O7Pol With piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2,2-Difluoro-2-phenylacetic acid With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; | 5 Resin 59 (0.075 mmol, 1 10 mg) was suspended in DMF (2 niL x 5 min) and mixed with a stream of 2 every 30 seconds. The Fmoc group was removed from the resin-supported building block by mixing the resin twice with a solution of 2% DBU, 2% piperidine in DMF (2 mL x 5 min) while agitating with a stream of 2 every 30 seconds. The resin was washed six times with DMF (2 mL x 30 sec). α,α-Difluorophenylacetic acid (34; 0.1 M solution in DMF, 2.5 mL, 3.3 equiv, 0.25 mmol), followed by HATU (0.2M solution in DMF, 1.15 mL, 3.1 equiv, 0.23 mmol) and N-methyl morpholine (1.0 M in DMF, 0.5 mL, 6.7 equiv, 0.5 mmol) were added to the resin. The reaction mixture was agitated by a stream of nitrogen for 30 min. The reagents were drained from the reaction vessel, and the resin was washed six times with DMF (2 mL x 30 sec) to yield 60. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C59H52Cl2N3O6Pol With piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2,2-Difluoro-2-phenylacetic acid With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; | 6 Resin 63 (0.150 mmol, 230 mg) was suspended in DMF (4 mL x 5 min) and mixed with a stream of 2 every 30 seconds. The Fmoc group was removed from the resin-supported building block by mixing the resin twice with a solution of 2% DBU, 2% piperidine in DMF (4 mL x 5 min) while agitating with a stream of 2 every 30 seconds. The resin was washed six times with DMF (4 mL x 30 sec). α,α-Difluorophenylacetic acid (34; 0.1 M solution in DMF, 3 mL, 2 equiv, 0.30 mmol), followed by HATU (0.2M solution in DMF, 3.15 mL, 2.1 equiv, 0.31 mmol) and N-methyl morpholine (1.0 M in DMF, 1.0 mL, 6.7 equiv, 1.0 mmol) were added to the resin. The reaction mixture was agitated by a stream of nitrogen for 30 min. The reagents were drained from the reaction vessel, and the resin was washed six times with DMF (4 mL x 30 sec) and six times with DCM (4 mL x 30 sec) to yield 64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 106.3 Synthesis of 2,2,2-trichloroethyl (1S,5aS,6R,11bR)-14-(2,2-difluoro-2-phenylacetyl)-10-methoxy-3a,4,5,6,7,11c-hexahydro-1H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indole-3(2H)-carboxylate (128) Under an argon atmosphere, the compound 127 (30 mg, 0.062 mmol) was dissolved in DMF (1 mL), the solution was added with 2,2-difluoro-2-phenylacetic acid (16 mg, 0.093 mmol), diisopropylethylamine (32 µL, 0.19 mmol), and O-(7-azabenzotriazol-1-yl)tetramethyluronium hexafluorophosphate (47 mg, 0.12 mmol), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate, water, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then concentrated to obtain a crude product of the title compound 128. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 50℃; for 12h; Inert atmosphere; | |
3% | In acetonitrile at 20℃; for 20h; Schlenk technique; Inert atmosphere; UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dipotassium peroxodisulfate In water; acetonitrile at 55℃; for 12h; Inert atmosphere; Schlenk technique; | |
76% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 72% 2: 12% | With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 24h; | |
75% | With dipotassium peroxodisulfate In water; acetonitrile at 55℃; for 12h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube 3.1: lithium hydroxide monohydrate / methanol / 12 h / 90 °C 4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 4.2: 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube 3.1: lithium hydroxide monohydrate / methanol / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube 3.1: lithium hydroxide monohydrate / methanol / 12 h / 90 °C 4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 4.2: 4 h / 0 - 20 °C 5.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube 3.1: lithium hydroxide monohydrate / methanol / 12 h / 90 °C 4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 4.2: 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube 3.1: lithium hydroxide monohydrate / methanol / 12 h / 90 °C 4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 4.2: 0.5 h / 0 - 20 °C 4.3: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube 3.1: lithium hydroxide monohydrate / methanol / 12 h / 90 °C 4.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: p-benzoquinone; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 140 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: 2,2-Difluoro-2-phenylacetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Stage #2: 8-amino quinoline With triethylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With 1-methyl-pyrrolidin-2-one; Ir[dF(CF3)ppy]2(dtbpy)BF4; 1-methoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one at 20℃; for 10h; Schlenk technique; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In tetrahydrofuran; ethyl acetate | N-(2-(2,6-diaminopyridin-4-yl)-2-phenylethyl)-2,2-difluoro-2-phenylacetamide To 4-(2-amino- 1 -phenylethyl)pyridine-2,6-diamine, HC1 (0.056 g, 0.210 mmol), TEA (0.176 mL, 1.260 mmol) and 2,2-difluoro-2-phenylacetic acid (0.036 g, 0.21 mmol) dissolved in THF (2.1 mL) was added T3P in EtOAc (0.25 mL, 0.42 mmol), and the mixture was stirred overnight. To this was added saturated NaHCO3, and the product wasextracted into EtOAc x2. The organics were dried over Na2SO4, filtered concentrated and purified via flash chromatography to furnish N-(2-(2,6-diaminopyridin-4-yl)-2- phenylethyl)-2,2-difluoro-2-phenylacetamide (0.05 8 g, 0.14 mmol, 67 % yield) contaminated with residual MeOH. MS (ESI) m/z 383.2. ‘H NMR (500 MHz, CDC13) ö 7.49 - 7.38 (m, 5H), 7.34 - 7.24 (m, 3H), 7.21 - 7.15 (m, 2H), 6.45 (br. s., 1H), 5.71 (s,2H), 4.18 (br. s., 4H), 3.98 - 3.91 (m, 1H), 3.90 - 3.81 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | In toluene at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 24h; | 2 (i?)-N-(l-(3-(3,4-dimethoxyphenyl)-2,6-dimethylimidazo[l,2- )]pyridazin-8- yl)pyrrolidin-3-yl)-2,2-difluoro-2-phenylacetamide (37) To a solution of la (320 mg, 0.8 mmol), DIPEA (0.6 mL, 4 mmol) and (0545) 2,2-difiuoro-2-phenylacetic acid (206 mg, 1.2 mmol) in DMF (10 mL) was added HATU (365 mg, 0.96 mmol) and reaction mixture was stirred for 24 h and then solvent was evaporated. Residue was chromatographed on silica gel column (150 g, toluene:ethyl acetate 2: 1). Fractions containing product were evaporated and re- chromatographed (120 g, toluene: acetone 8: 1) to afford product (202 mg, 48%). Solids were re-cry stalized from ethyl acetate in freezer. [Jf? - 0 (c 0.224, (0546) CHCy/H NMR (400 MHz, d6-DMSO) δ 1.95 - 2.08 (m, 1H), 2.16 - 2.27 (m, 1H), 2.29 (s, 3H), 2.39 (s, 3H), 3.78 (s, 3H), 3.81 (s, 3H), 3.89 (br s, 3H), 4.14 (br s, 1H),4.41 - 4.51 (m, 1H), 5.81 (s, 1H), 7.07 (d, J = 8.5 Hz, 1H), 7.17 (dd, J = 8.3, 2.0 Hz, 1H), 7.28 (d, J = 2.0 Hz, 1H), 7.66 - 7.45 (m, 5H), 9.29 (d, J = 6.8 Hz, 1H). 1 C NMR (101 MHz, d6-DMSO) δ 15.0, 21.7, 30.2, 47.8, 49.4, 54.1, 55.7, 94.1, 111.8, 113.2, 114.9 (t, J= 250.8 Hz), 122.0, 123.9, 125.4 (t, J = 5.9 Hz), 129.0, 133.4 (t, J = 25.6 Hz), 131.18, 136.6, 141.1, 148.3, 148.4, 163.6 (t, J = 31.3 Hz), 163.31. HRMS calcd for C28H30F2N5O3 m/z: 522.2311 (M+H)+, found 522.2203. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C29H31F14NOSi In acetonitrile at -5℃; for 16h; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 3.5h; | 43 Example 43: (S)-5-chloro-N-(2-(1 -(2,2-difluoro-2-phenylacetyl)piperidin-4-yl)-1 -(6- methoxypyridin-3-yl)ethyl)thio hene-2-carboxamide A solution of (S)-5-chloro-N-(1 -(6-methoxypyridin-3-yl)-2-(piperidin-4-yl)ethyl)thiophene-2- carboxamide hydrochloride (40 mg, 0.080 mmol) in DMF (0.8 mL) was treated with 2,2- difluoro-2-phenylacetic acid (15 mg, 0.088 mmol), DIEA (0.042 mL, 0.24 mmol), HATU (46 mg, 0.120 mmol), and stirred at RT for 3.5 hours. The reaction was quenched with 2M NH3/MeOH and stirred for an additional 45 min. The mixture was diluted with water and extracted with EtOAc. The EtOAc solution was washed with 1 N HCI, saturated aqueous NaHC03, brine, dried over Na2S04, filtered, and concentrated. Purification by reverse phase HPLC (C18, 30-100% MeCN/water with 0.1 % formic acid) afforded the title compound (24 mg, 55 % yield) as white solid. LCMS (ESI) m/z calcd for C26H26CIF2N3O3S: 533.1. Found: 534.3 (M+1)+. NMR (400MHz, CDCI3) δ 8.14 (br s, 1H), 7.64 - 7.38 (m, 6H), 7.22 (d, J = 3.5 Hz, 1H), 6.88 (d, J = 3.9 Hz, 1H), 6.75 (d, J = 8.6 Hz, 1H), 5.96 (br s, 1H), 5.26 - 5.04 (m, 1H), 4.73 - 4.46 (m, 1H), 4.06 - 3.79 (m, 4H), 2.91 - 2.50 (m, 2H), 1.96 - 1.67 (m, 4H), 1.56 - 1.38 (m, 1H), 1.34 - 1.09 (m, 1H), 1.07 - 0.76 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With ammonium peroxydisulfate; palladium diacetate; acetic acid In water; dimethyl sulfoxide at 55℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; silver perchlorate In dichloromethane at 20℃; for 3h; Electrolysis; Molecular sieve; | General procedure for decarboxylative etherification. General procedure: With no precautions to exclude air or moisture, the ElectraSyn vial (5 ml) with a stir bar was charged with carboxylic acid (0.2 mmol, 1.0 equiv.), alcohol (0.6 mmol, 3.0 equiv.), 2,4,6-collidine (0.6 mmol, 3.0 equiv.), nBu4NPF6 (0.3 mmol, 1.5 equiv.), 3 Å molecular sieves (150 mg), AgPF6 (0.3 mmol, 1.5 equiv.) and CH2Cl2 (3.0 ml). The ElectraSyn vial cap equipped with anode (graphite) and cathode (graphite) were inserted into the mixture. After pre-stirring for 15 min, the reaction mixture was electrolysed at a constant current of 10 mA for 3 h. The ElectraSyn vial cap was removed, and electrodes were rinsed with Et2O (2 ml), which was combined with the crude mixture. Then, the crude mixture was further diluted with Et2O (30 ml). The resulting mixture was washed with 2 M HCl (20 ml) and NaHCO3 (aq.) (20 ml), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by preparative thin-layer chromatography to furnish the desired product. Full experimental details and characterization of new compounds can be found in the Supplementary Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; silver perchlorate; In dichloromethane; at 20℃; for 3h;Electrolysis; Molecular sieve; | General procedure: With no precautions to exclude air or moisture, the ElectraSyn vial (5 ml) with a stir bar was charged with carboxylic acid (0.2 mmol, 1.0 equiv.), alcohol (0.6 mmol, 3.0 equiv.), 2,4,6-collidine (0.6 mmol, 3.0 equiv.), nBu4NPF6 (0.3 mmol, 1.5 equiv.), 3 A molecular sieves (150 mg), AgPF6 (0.3 mmol, 1.5 equiv.) and CH2Cl2 (3.0 ml). The ElectraSyn vial cap equipped with anode (graphite) and cathode (graphite) were inserted into the mixture. After pre-stirring for 15 min, the reaction mixture was electrolysed at a constant current of 10 mA for 3 h. The ElectraSyn vial cap was removed, and electrodes were rinsed with Et2O (2 ml), which was combined with the crude mixture. Then, the crude mixture was further diluted with Et2O (30 ml). The resulting mixture was washed with 2 M HCl (20 ml) and NaHCO3 (aq.) (20 ml), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by preparative thin-layer chromatography to furnish the desired product. Full experimental details and characterization of new compounds can be found in the Supplementary Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; silver perchlorate In dichloromethane at 20℃; for 3h; Electrolysis; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; silver perchlorate In dichloromethane at 20℃; for 3h; Electrolysis; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With ammonium peroxydisulfate; silver nitrate In dichloromethane; water at 50℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 50℃; for 12h; Inert atmosphere; | |
52% | With dipotassium peroxodisulfate; silver carbonate In water at 60℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With dipotassium hydrogenphosphate; 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridin-10-ium tetrafluoroborate In N,N-dimethyl-formamide at 25℃; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4% | Stage #1: benzyl 2-{bis[(tert-butoxy)carbonyl]amino}prop-2-enoate With dipotassium hydrogenphosphate; 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridin-10-ium tetrafluoroborate In N,N-dimethyl-formamide for 0.333333h; Sealed tube; Inert atmosphere; Stage #2: 2,2-Difluoro-2-phenylacetic acid In N,N-dimethyl-formamide at 25℃; for 20h; Inert atmosphere; Sealed tube; Irradiation; Stage #3: trifluoroacetic acid In dichloromethane at 25℃; for 1.5h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With Iron(III) nitrate nonahydrate; ammonium peroxydisulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; |
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