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[ CAS No. 185739-14-4 ] {[proInfo.proName]}

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Chemical Structure| 185739-14-4
Chemical Structure| 185739-14-4
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Product Details of [ 185739-14-4 ]

CAS No. :185739-14-4 MDL No. :MFCD27946567
Formula : C9H8F2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :ZQLLPWMNXQYESO-UHFFFAOYSA-N
M.W :234.22 Pubchem ID :10977366
Synonyms :

Safety of [ 185739-14-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501 UN#:1760
Hazard Statements:H302-H315-H318-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 185739-14-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 185739-14-4 ]

[ 185739-14-4 ] Synthesis Path-Downstream   1~63

  • 1
  • [ 433-06-7 ]
  • [ 185739-14-4 ]
YieldReaction ConditionsOperation in experiment
97% With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -65℃; for 0.5h; To a 3-necked flask with a stir bar (oven dried), water-cooled condenser, and internal thermometer was added 2,2,2-trifluoroethyl-4-methylbenzenesulfonate (25.4 g, 100 mmol) followed by THF (333 mL, 0.3 M). The mixture was stirred and cooled in an acetone/dry-ice bath (internal temperature at -78 C.). nBuLi (10 M in hexanes, 20 mL, 200 mmol) was added via a syringe over 10 min with internal temperature at about -65 C. The reaction mixture turned to a dark color and was stirred at -78 C. for 20 min. A mixture of water (50 mL) and THF (50 mL) was added dropwise via an addition funnel to quench the reaction (maintained internal temperature at about -70 C.). The mixture was warmed to ambient temperature and ethyl acetate (400 mL) was added. The organic layer was separated and the aqueous layer extracted with ethyl acetate (2×80 mL). The combined organics were washed with brine (50 mL), dried over Na2SO4 and evaporated to give a dark oil (29.3 g) that was purified on silica (220 g column, 60 mL/min) with gradients from 100% heptane to 40% ethyl acetate-60% heptane to give the title product as a colorless oil (22.73 g, 97% yield). 1H NMR (400 MHz, chloroform-d) 6 ppm 7.83 (d, J=8.31 Hz, 2H) 7.39 (d, J=8.19 Hz, 2H) 6.09 (dd, J=14.31, 3.91 Hz, 1H) 2.48 (s, 3H). 19F NMR (376 MHz, chloroform-d) δ ppm -92.88--88.40 (m, 1F) -110.58--107.12 (m, 1F). The title product did not ionize in LCMS
With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 2h; 1.4. Interm F Toluene-4-sulfonic acid 2,2,2-trifluoroethyl ester (1 eq, 6.0 g) is dissolved in anhydrous THF (120 mL). The reaction is cooled down to -78C, after which n-butyllithium (2.5M in hexane, 2.3 eq, 22 mL) is carefully added. The reaction is left stirring at this temperature for 2 h, after which the mixture is diluted with water and EtOAc. Extraction with EtOAc (3 x 100 mL) is performed. The combined organics are washed with sat. brine and dried over anhydrous Na2S04. Purification of the crude through column chromatography (silica, petroleum ether/EtOAc; 95:5 to 80:20) yields the desired product.
26.9 mmol With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 0.333333h; A solution of 2,2,2-trifluoroethyl tosylate (33.4 mmol) inanhydrous THF (111 mL), at -78 C, and n-butyllithiumsolution (11 M in hexane, 66.9 mmol) was stirred at -78 Cfor 20 mm, then quenched with a mixture of water (20 mL)and THF (20 mL) whilst maintaining internal temperature at -60 C, then warmed to RT and extracted with EtOAc. The combined organic extracts were washed with a saturated solution of brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification gave the titled compound (26.9 mmol) as a colourless oil. 1H NMR (400MHz, DMSO-d6, ): 7.86 (d, J = 8.4 Hz, 2H), 7.54 (d, J = 8.6 Hz, 2H), 6.85 (dd, J = 15.6, 3.9 Hz, 1 H), 2.45 (5, 3H).
2.4 g With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 0.666667h;Inert atmosphere; 2,2,2-trifluoroethyl p-methylbenzenesulfonate (11-1) (2.57 g, 10.0 mmol) was dissolved in tetrahydrofuran (15 mL), the reaction solution was cooled to -78C under protection of nitrogen, and n-butyllithium (2.5 M in hexane, 8 mL, 20 mmol) was slowly dropwise added. The reaction solution was stirred at -78C for 40 minutes, and water (4.5 g, 25 mmol) and tetrahydrofuran (10 mL) were slowly dropwise added. The reaction solution was slowly warmed to room temperature. The reaction was added with water (60 mL), and extracted with ethyl acetate (30 mL*2). The organic phase was collected, washed with saturated sodium chloride solution (50 mL*2), dried over anhydrous sodium sulfate, filtered to remove anhydrous sodium sulfate, concentrated under reduced pressure, followed by purification through column chromatography, and the target compound 2.4 g was obtained. ESI-MS (m/z): 235.1 [M + H]+.
With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 1h; To a solution of 172.1 (25 g, 98.34 mmol, 1.0 equiv) in THF (250 mL), was added n-butyl lithium (2.5M in Hexane) (78.6 mL, 196.68 mmol, 2.0 equiv) at -78 C and stirred for 1 h. A saturated solution of ammonium chloride was added slowly to quench the reaction. The mixture was allowed to warmed to room temperature and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (CombiFlash, 3% ethyl acetate in hexane) to afford 172.2. 1H NMR (CDCl3, 400 MHz): δ 7.84-7.82 (d, J= 8 Hz, 2H), 7.41-7.39 (d, J = 8 Hz, 2H), 6.11-6.07 (m, 1H), 2.49 (s, 3H).

  • 2
  • [ 185739-14-4 ]
  • sodium 1,1-difluoro-2-tosyloxyethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With sodium hydrogensulfite; dibenzoyl peroxide In methanol; water at 80℃; for 40h; 9 9.3 g of 2,2-difluoroethenyl tosylate, which had been synthesised by a conventional technique, was dispersed in 17 g of water and 37 g of methanol, after which 4.7 g of sodium hydrogen sulfite and 0.5 g of benzoyl peroxide were added. The reaction mixture was stirred at 80°C for 40 hours. The reaction solution was allowed to cool, after which methanol was distilled off in vacuum. Toluene was added, followed by separatory operation to separate a water layer. A saturated sodium chloride aqueous solution was added to the water layer whereupon white crystals settled out. The crystals were collected by filtration, washed with a small volume of saturated sodium chloride aqueous solution and then dried in vacuum, obtaining the target compound, sodium 1,1-difluoro-2-tosyloxyethanesulfonate. White crystals, 2.5 g (yield 16%). The target compound was analyzed by spectroscopy. The NMR spectra, 1H-NMR (300 MHz in D2O) and 19F-NMR (282 MHz in D2O (shift standard CF3CO2D)) are shown in FIGS. 1 and 2. Infrared absorption spectra (IR, KBr, cm-1) 3041, 2994, 1598, 1452, 1363, 1307, 1292, 1280, 1238, 1213, 1197, 1182, 1130, 1112, 1105, 1022, 973, 939, 842, 809, 759, 649
  • 3
  • [ 905966-40-7 ]
  • [ 185739-14-4 ]
  • [ 1022094-52-5 ]
  • 4
  • [ 1022094-44-5 ]
  • [ 185739-14-4 ]
  • [ 1022094-53-6 ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 19h;
  • 5
  • [ 5122-94-1 ]
  • [ 185739-14-4 ]
  • [ 1022094-45-6 ]
YieldReaction ConditionsOperation in experiment
98% With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 70℃; for 22h;
  • 6
  • [ 126747-14-6 ]
  • [ 185739-14-4 ]
  • [ 38936-00-4 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 18h;
  • 7
  • [ 185739-14-4 ]
  • [ 149104-90-5 ]
  • 1-(4-(2,2-difluorovinyl)phenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 18h;
  • 8
  • [ 185739-14-4 ]
  • [ 171364-85-5 ]
  • [ 1022094-54-7 ]
YieldReaction ConditionsOperation in experiment
72% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 18h; Inert atmosphere; Sealed tube;
69% With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 19h;
  • 9
  • [ 185739-14-4 ]
  • [ 627906-96-1 ]
  • [ 131581-40-3 ]
  • 10
  • [ 185739-14-4 ]
  • 5,5-dimethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborinane [ No CAS ]
  • [ 220676-10-8 ]
YieldReaction ConditionsOperation in experiment
94% With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 70℃; for 22h;
  • 11
  • [ 445264-61-9 ]
  • [ 185739-14-4 ]
  • [ 1022094-53-6 ]
  • 12
  • [ 1052686-60-8 ]
  • [ 185739-14-4 ]
  • 5-(2,2-difluorovinyl)-2-methoxypyrimidine [ No CAS ]
  • 14
  • [ 871-91-0 ]
  • [ 185739-14-4 ]
  • 10,10-difluorodec-9-en-7-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
  • 15
  • [ 32870-98-7 ]
  • [ 185739-14-4 ]
  • 9-(4,4-difluorobut-3-en-1-yn-1-yl)phenanthrene [ No CAS ]
  • 16
  • [ 1315350-04-9 ]
  • [ 185739-14-4 ]
  • 4-amino-3-(2,2-difluorovinyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 60℃; for 1h; Inert atmosphere; 1.5.2.ii Step ii): 4-Amino-3-(2,2-difluorovinyl)benzonitrile Step ii): 4-Amino-3-(2,2-difluorovinyl)benzonitrile 4-Amino-3-(4,4,5,5-tetramethyl[l,3,2]dioxaborolan-2-yl)benzonitrile (1 eq, 30.7 mmol) and toluene-4-sulfonic acid 2,2-difluorovinyl ester (1 eq, 7.2 g) are dissolved in a 4: 1 solution of dioxane and water (175 mL). Pd(dba)3 (0.05 eq, 1.4 g), HBF4PCy3 (0.1 eq, 1.1 g) and potassium phosphate (3 eq, 19.6 g) are added, after which the suspension is degassed under nitrogen atmosphere for 10 min and the reaction is brought to 60°C for 1 h. The suspension is then filtered over a Celite pad and concentrated in vacuo. The residue is dissolved in EtOAc and an aq. extraction with sat. NaHCOs and EtOAc (3 x 150 mL) is performed. The combined organics are washed with sat. brine, dried over Na2S04 and concentrated. Purification of the crude through column chromatography (silica, petroleum ether/EtOAc; 95:5 to 90: 10) yields the desired product.
  • 17
  • (2R)-8-fluoro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one [ No CAS ]
  • [ 185739-14-4 ]
  • (2R)-6-(2,2-difluoroethenyl)-8-fluoro-2-methyl-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: (2R)-8-fluoro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one; toluene-4-sulfonic acid 2,2-difluorovinyl ester With potassium phosphate In 1,4-dioxane for 0.166667h; Inert atmosphere; Sonication; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 105℃; for 4h; Inert atmosphere; Sealed tube; 179 (2i? -6-(2,2-Difluoroethenvn-8-fluoro-2-methyl-4 (l,3.5-trimethyl-lH-pyrazol-4-yl - methyl]-3,4-dihydro-2H-l,4-benzoxazin-3-one An aqueous solution of tripotassium phosphate (1.27M, 1.43 mL) was added to a solution of 2,2-difluoroethenyl 4-methylbenzene-l -sulfonate (prepared according to the procedure described in J. Org. Chem., 2008, 73, 3404) (250 mg, 1.07 mmol) and Intermediate 150 (76%, 603 mg, 1.07 mmol) in 1,4-dioxane (7 mL). The mixture was degassed with a stream of bubbling nitrogen whilst being sonicated for 10 minutes. Tris(dibenzylidineacetone)dipalladium(0) (24.44 mg, 0.03 mmol) and tricyclohexyl- phosphonium tetrafluoroborate (19.65 mg, 0.05 mmol) were added under nitrogen and the mixture was heated, whilst stirring, at 105°C in a sealed tube for 4 h. The mixture was allowed to cool to r. , then partitioned between saturated aqueous Na2C03 solution (30 mL) and EtOAc (30 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with brine (20 mL), dried over MgS04, filtered and concentrated in vacuo. Purification of the crude residue by column chromatography, using 0-100% EtOAc in heptane, gave the title compound (322 mg, 55%). δΗ (500 MHz, DMSO-d6) 6.98 (dd, J 11.4, 1.7 Hz, IH), 6.87 (s, IH), 5.72 (dd, J27.3, 3.9 Hz, IH), 5.08 (d, J 15.9 Hz, IH), 4.90 (q, J6.7 Hz, IH), 4.84 (d, J 15.8 Hz, IH), 3.57 (s, 3H), 2.17 (s, 3H), 1.96 (s, 3H), 1.50 (d, J 6.7 Hz, 3H).Method B HPLC-MS: MH+ mlz 366.1, RT 2.01 minutes (100%).
  • 18
  • [ 6971-74-0 ]
  • [ 185739-14-4 ]
  • (E)-(3-oxo-2-tosylisoindolin-1-ylidene)methyl 4-methylbenzenesulfonate [ No CAS ]
  • 19
  • [ 6971-74-0 ]
  • [ 185739-14-4 ]
  • C23H20FNO6S2 [ No CAS ]
  • 20
  • [ 101251-09-6 ]
  • [ 185739-14-4 ]
  • N-(4-(2,2-difluorovinyl)phenyl)acteamide [ No CAS ]
  • 21
  • [ 6999-03-7 ]
  • [ 185739-14-4 ]
  • C11H14F2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 22
  • 1-bromo-4-(trans-4-n-propylcycohexyl)benzene [ No CAS ]
  • [ 185739-14-4 ]
  • C17H22F2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 23
  • [ 51554-95-1 ]
  • [ 185739-14-4 ]
  • C13H16F2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 24
  • [ 6343-72-2 ]
  • [ 185739-14-4 ]
  • C14H10F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 25
  • [ 66107-30-0 ]
  • [ 185739-14-4 ]
  • 4-(2,2-difluorovinyl)phenyl trifluoromethanesulfonate [ No CAS ]
  • 26
  • [ 6324-15-8 ]
  • [ 185739-14-4 ]
  • 4-(2,2-difluorovinyl)phenyl 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 27
  • [ 619-42-1 ]
  • [ 185739-14-4 ]
  • [ 1022094-52-5 ]
YieldReaction ConditionsOperation in experiment
90% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 28
  • [ 148547-19-7 ]
  • [ 185739-14-4 ]
  • C11H10F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 100℃; for 16h;
  • 29
  • [ 33626-98-1 ]
  • [ 185739-14-4 ]
  • C14H10F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 30
  • [ 580-13-2 ]
  • [ 185739-14-4 ]
  • [ 131581-40-3 ]
YieldReaction ConditionsOperation in experiment
96% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 31
  • [ 90-90-4 ]
  • [ 185739-14-4 ]
  • C15H10F2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 32
  • [ 3466-32-8 ]
  • [ 185739-14-4 ]
  • 1-(2,2-difluorovinyl)-4-(methylsulfonyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 33
  • [ 1127562-54-2 ]
  • [ 185739-14-4 ]
  • C17H11F2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 34
  • [ 4923-87-9 ]
  • [ 185739-14-4 ]
  • C10H6F2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 35
  • [ 92-66-0 ]
  • [ 185739-14-4 ]
  • [ 1022094-45-6 ]
YieldReaction ConditionsOperation in experiment
91% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 36
  • [ 86-76-0 ]
  • [ 185739-14-4 ]
  • 2-(2,2-difluorovinyl)dibenzo[b,d]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 37
  • [ 63996-36-1 ]
  • [ 185739-14-4 ]
  • 2-(4-(2,2-difluorovinyl)phenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 38
  • [ 92-86-4 ]
  • [ 185739-14-4 ]
  • 4,4'-bis-(2,2-difluorovinyl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 39
  • [ 179866-74-1 ]
  • [ 185739-14-4 ]
  • C28H22F4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 40
  • [ 866769-99-5 ]
  • [ 185739-14-4 ]
  • C34H26F4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 41
  • C34H51BrO2 [ No CAS ]
  • [ 185739-14-4 ]
  • C36H52F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 42
  • [ 2113-57-7 ]
  • [ 185739-14-4 ]
  • 3-(2,2-difluorovinyl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 43
  • C19H23BrO7 [ No CAS ]
  • [ 185739-14-4 ]
  • C21H24F2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 44
  • [ 185739-14-4 ]
  • [ 2925-16-8 ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: (2,2-difluoroethenyl) 4-methylbenzenesulfonate With [2,2]bipyridinyl; nickel (II) chloride; zinc In N,N-dimethyl acetamide at 60℃; for 8h; Stage #2: With iodine for 0.333333h;
51% Stage #1: (2,2-difluoroethenyl) 4-methylbenzenesulfonate With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; nickel(II) bromide; zinc In N,N-dimethyl acetamide at 60℃; for 4h; Sealed tube; Stage #2: With iodine; lithium chloride In tetrahydrofuran at 20℃; for 0.333333h;
  • 45
  • [ 4333-76-0 ]
  • [ 185739-14-4 ]
  • C16H12F2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 46
  • [ 185739-14-4 ]
  • [ 4714-24-3 ]
  • C16H12F2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 47
  • [ 5111-65-9 ]
  • [ 185739-14-4 ]
  • [ 1022094-48-9 ]
YieldReaction ConditionsOperation in experiment
89% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 48
  • [ 101-55-3 ]
  • [ 185739-14-4 ]
  • [ 220676-10-8 ]
YieldReaction ConditionsOperation in experiment
91% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 49
  • [ 36809-26-4 ]
  • [ 185739-14-4 ]
  • [ 1501969-17-0 ]
YieldReaction ConditionsOperation in experiment
91% With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;
  • 50
  • [ 17870-62-1 ]
  • [ 185739-14-4 ]
  • 2-fluoro-indolizine-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 12h; 1.b.2 b) Step-2: Ethyl 2-fluoroindolizine-3-carboxylate: To a stirred solution of 1-(2-ethoxy-2-oxoethyl)pyridin-1-ium (8 g, 48.1 mmol)in N,N-dimethyl formamide (80 mL), 2,2-difluorovinyl 4-methylbenzenesulfonate (7.9 g, 33.7 mmol), potassium carbonate (6.7 g, 48.1 mmol) and triethyl amine (6.7 mL, 48.1 mmol) were added. The reaction mixture was heated at 70 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (150 mL) was added to the above reaction mixture and extracted twice with ethyl acetate (300 mL). The combined ethyl acetate layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash column chromatography on silica gel using ethyl acetate in hexane as an eluent to obtain ethyl 2- fluoroindolizine-3-carboxylate (4.2 g, 20.3 mmol, 42 % yield). 1H-NMR (400 MHz, DMSO-d6) d 9.29 (dq, J = 7.2, 1.0 Hz, 1H), 7.51-7.65 (m, 1H), 7.23-7.27 (m, 1H), 6.72-7.08 (m, 1H), 6.27-6.50 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H); ESI MS (m/z) 208.20 (MH)+
  • 51
  • methyl 4-(2,2-difluorocyclopropyl)benzoate [ No CAS ]
  • [ 185739-14-4 ]
  • C13H11F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 52
  • methyl 3-(2,2-difluorocyclopropyl)benzoate [ No CAS ]
  • [ 185739-14-4 ]
  • C13H11F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 53
  • C15H17F2NO [ No CAS ]
  • [ 185739-14-4 ]
  • C17H18F3NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 54
  • C10H10F2O2S [ No CAS ]
  • [ 185739-14-4 ]
  • C12H11F3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 55
  • 2-(2,2-difluorocyclopropyl)naphthalene [ No CAS ]
  • [ 185739-14-4 ]
  • C15H11F3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 56
  • 2-(4-(2,2-difluorocyclopropyl)phenyl)pyridine [ No CAS ]
  • [ 185739-14-4 ]
  • C16H12F3N [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 57
  • (8R,9S,13S,14S)-3-(2,2-difluorocyclopropyl)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one [ No CAS ]
  • [ 185739-14-4 ]
  • C23H25F3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 58
  • C20H26F2O2 [ No CAS ]
  • [ 185739-14-4 ]
  • C22H27F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 59
  • C22H28F2O6 [ No CAS ]
  • [ 185739-14-4 ]
  • C24H29F3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 60
  • C14H16F2O2 [ No CAS ]
  • [ 185739-14-4 ]
  • C16H17F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 61
  • [ 1323437-13-3 ]
  • [ 185739-14-4 ]
  • C17H13F3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 62
  • C16H14F2O3S [ No CAS ]
  • [ 185739-14-4 ]
  • C18H15F3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
  • 63
  • [ 1241957-35-6 ]
  • [ 185739-14-4 ]
  • C15H17F3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;
Same Skeleton Products
Historical Records