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[ CAS No. 769965-95-9 ]

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2D
Chemical Structure| 769965-95-9
Chemical Structure| 769965-95-9
Structure of 769965-95-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 769965-95-9 ]

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Related Doc. of [ 769965-95-9 ]

SDS

Product Details of [ 769965-95-9 ]

CAS No. :769965-95-9MDL No. :MFCD13195329
Formula : C10H8FNO Boiling Point : 351.8±42.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :177.18Pubchem ID :58398965
Synonyms :

Computed Properties of [ 769965-95-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 769965-95-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 769965-95-9 ]

  • Downstream synthetic route of [ 769965-95-9 ]

[ 769965-95-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 56341-41-4 ]
  • (2-bromoethyl)(diphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]
  • [ 769965-95-9 ]
YieldReaction ConditionsOperation in experiment
78% General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.
  • 2
  • [ 56341-41-4 ]
  • diphenyl(vinyl)sulfonium trifluoromethanesulfonate [ No CAS ]
  • [ 769965-95-9 ]
  • 3
  • [ 769965-95-9 ]
  • {5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl methanesulfonate [ No CAS ]
  • 1'-({5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl)-5'-fluorospiro[cyclopropane-1,3'-indol]-2'(1'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 0.5h; A mixture of {5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl methanesulfonate (183 mg, 0.50 mmol), cesium carbonate (325 mg, 1.0 mmol) and <strong>[769965-95-9]5'-fluorospiro[cyclopropane-1,3'-indol]-2'(1'H)-one</strong> (79 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL) was heated with stirring at 60C for 30 minutes. The resulting mixture was purified by preparative HPLC to afford the title product.
  • 4
  • [ 769965-95-9 ]
  • [ 1319743-48-0 ]
  • [ 1319742-72-7 ]
YieldReaction ConditionsOperation in experiment
Example 2.5Trans-2-chloro-N-{-4-((5'-fluoro-2'-oxospiro[cyclopropane-1 ,3'-indoline]-1 yl)methyl)cyctohexyl}-5-(trifluoromethyl)benzamide 5'-Fluorospiro[cyclopropane-1 ,3'-indolin]-2'-one (Intermediate H) {67 mg, 0.378 mmol) in dry D F (3 ml) was treated with NaH {60% in mineral oil) (15.12 mg, 0.378 mmol) under N2 and the contents left stirring for ~10 mins. After this time, trans- methanesulfonic acid 4-{2-chloro-5-trifluoromethyl-benzoylamino)-cyclohexyl methyl ester (Intermediate C) (105 mg, 0.253 mmol) was added and the solution heated to 70C for 2.5 h. After cooling to RT overnight, the mixture was diluted with EtOAc/H20 (40 ml) and transferred to a separating funnel. The organic layer was separated and washed with brine, dried (MgS04), and concentrated in vacuo to give a light brown oil. The crude oil was chromatographed on silica eluting with a gradient of 0%-30% EtOAc/iso-hexane follwed by an isocratic gradient of 30% EtOAc/iso-hexane to afford the title compound as a white solid; LC-MS Rt= 1.36 mins; [M+H]+ 495.3; Method = 2minl_C_30_v002. 1H NMR (400 MHz, CDCI3). delta 7.90 (1H, s), 7.55 (1 H, d), 7.50 (1H, d), 6.95 (1H, m), 6.80 (1 H, m), 6.60 (1H, m), 5.95 (1 H, d), 4.0 (1H, m), 3.65 (2H, d), 2.20 (2H, m), 1.85 (5H, m), 1.55 (2H, m), 1.25 (4H, m).
  • 5
  • [ 56341-41-4 ]
  • [ 106-93-4 ]
  • [ 769965-95-9 ]
YieldReaction ConditionsOperation in experiment
Intermediate H5'-F I uorospiro[cyc I op ropane-1 3'-i ndol i n]-2'-one5-Fluoroindolin-2-one (500 mg, 3.31 mmol) was dissolved in dry THF (30 ml). To this was added N1 ,N1,N2,N2-tetramethylethane-1,2-diamine (1.091 ml, 7.28 mmol) and the mixture was cooled to -78C. BuLi (1.6M in Hexanes) (4.14 ml, 6.62 mmol) was added dropwise and the contents left stirring for 20 mins. 1 ,2-Dibromoethane (0.342 ml, 3.97 mmol) was added dropwise and the mixture was stirred at -78C for 30 mins and allowed to warm to RT overnight. The reaction was quenched by addition of NH CI (20 ml) and extracted into EtOAc. The solvent was removed in vacuo and purification by chromatography on silica eluting with acetone/iso-hexane afforded the title compound as a white solid; 1H NMR (400 MHz, CDCI3) delta 8.40 (1H, s), 6.90 (2H, m), 6.60 (1 H, d), 1.80 (2H, m), 1.55 (2H, m).
  • 9
  • [ 769965-94-8 ]
  • [ 769965-95-9 ]
YieldReaction ConditionsOperation in experiment
96% With trifluoroacetic acid; at 60℃; A solution of 5-fluoro-1-(4-methoxy-benzyl)-siprocyclopropyloxindole (3. 38 g, 11.4 mmol) in TFA (20 mL) was stirred at 60 C overnight. The solvent was then removed and the reaction was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 until the washings were neutral. The organic phase was then washe with brine, dried over Na2S04 and the solvent was removed. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 1.94 g (96%) of <strong>[769965-95-9]5-fluoro-siprocyclopropyloxindole</strong> ; 1H NMR (MeOD, 400 MHz) os 1. 76-1.86 (m, 4H), 6.91- 6.94 (m, 1H), 7.07-7. 11 (m, 2H); HPLC-MS calcd. for CloHsFNO (M +H 178.2, found 178.3.
96% With trifluoroacetic acid; at 60℃; A solution of 5-fluoro-1-(4-methoxy-benzyl)-siprocyclopropyloxindole (3.38 g, 11.4 mmol) in TFA (20 mL) was stirred at 60 C overnight. The solvent was then removed and the reaction was diluted with ethyl acetate and washed with saturated aqueous NAHCO3 until the washings were neutral. The organic phase was then washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 1.94 g (96%) of 5-FLUOR- siprocyclopropyloxindole
  • 10
  • [ 769965-95-9 ]
  • 5’-fluorospiro[cyclopropane-1,3’-indoline] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; at 0 - 50℃; for 3.25h; A sample of <strong>[769965-95-9]5-fluoro-siprocyclopropyloxindole</strong> (172 mg, 97 jimol) was cooled in an ice/water bath and treated with a 1.0 M solution of LAH (1.94 ml, 1.9 mmol). The reaction was stirred at room temperature for 15 minutes and then at 50 C for 3 hours and finally was cooled back down with an icelwater bath. The reaction was treated with 1 M NaOH (1.9 mL) followed by water (1.9 mL). The reaction was filtered over celite and dried over MgS04. After filtration, the solvent was removed and the crude material of 5-fluoro- siprocyclopropylindoline was used without purification.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 50℃; for 3h; A sample of <strong>[769965-95-9]5-fluoro-siprocyclopropyloxindole</strong> (172 mg, 97 NMOL) was cooled in an ice/water bath and treated with a 1.0 M solution of LAH (1.94 ml, 1.9 mmol). The reaction was stirred at room temperature for 15 minutes and then at 50 C for 3 hours and finally was cooled back down with an ICE/WATER bath. The reaction was treated with 1 M NAOH (1.9 mL) followed by water (1.9 mL). The reaction was filtered over celite and dried over MGS04. After filtration, the solvent was removed and the crude material of 5-fluoro- siprocyclopropylindoline was used without purification.
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