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[ CAS No. 91524-70-8 ]

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Chemical Structure| 91524-70-8
Chemical Structure| 91524-70-8
Structure of 91524-70-8 * Storage: {[proInfo.prStorage]}

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Product Details of [ 91524-70-8 ]

CAS No. :91524-70-8 MDL No. :MFCD09801042
Formula : C7H6BrFS Boiling Point : 227.2±30.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :221.09 g/mol Pubchem ID :-
Synonyms :

Safety of [ 91524-70-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 91524-70-8 ]

  • Downstream synthetic route of [ 91524-70-8 ]

[ 91524-70-8 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 1003-98-1 ]
  • [ 4856-13-7 ]
  • [ 91524-70-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; sodium nitrite 1.) H2O, 4 deg C, 2.) -> RT, 0.5 h; Yield given. Multistep reaction;
Stage #1: 2-bromo-4-fluoroaniline With sulfuric acid; sodium nitrite In water at 0 - 25℃; Stage #2: cuprous methylmercaptide In water at 25℃; for 1h; 19.19.1 Examplel9. 19: Preparation of 5-{r-[3-bromo-4-(methylsulfonyl)phenyl]-4,4'-bipiperidin-l-yl}-NN- dimethyl- 1 ,2,4-thiadiazol-3 -amine; Step 1 : 2-bromo-4-fluorophenyl methyl sulfide; A 00C solution of 2-bromo-4-fluoroaniline (1.50g; 7.89mmol) in 25% aq H2SO4 (2OmL) was treated with sodium nitrite (583mg; 8.45mmol). The solution was warmed to 25°C and added to a suspension of CuSCH3 (6.1 Ig; 55.3mmol) in water (5OmL). The mixture was stirred at 25°C for lhr, then extracted with iPrOAc. The organic was dried over magnesium sulfate, filtered and evaporated to a red oil. Chromatography (Horizon; 0% to 20% MTBE/hex; linear gradient)) afforded the title compound.
  • 2
  • [ 91524-70-8 ]
  • [ 1039744-23-4 ]
YieldReaction ConditionsOperation in experiment
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 18h; 19.19.2 Step 2: 2-bromo-4-fluorophenyl methyl sulfone; A solution of 2-bromo-4-fiuorophenyl methyl sulfide (614mg; 2.78mmol) in CH2Cl2 (1OmL) was treated with mCPBA (1.278g; 75wt%; 5.55mmol). The mixture was stirred at 25°C for 18hr. The mixture was filtered and washed with aq. sodium bicarbonate. The organic was dried over magnesium sulfate, filtered and evaporated to a solid. The solid was chromatographed (PTLC; 2: 1 hex/MTBE), affording the title compound.
  • 3
  • [ 91524-70-8 ]
  • 4-fluoro-2-iodo-1-(methylsulfanyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 2-bromo-4-fluoro-1-(methylsulfanyl)benzene With magnesium In tetrahydrofuran at 20 - 50℃; for 16h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; 4-fluoro-2-iodo-1 -(methylsulfanyl)benzene 2-Bromo-4-fluoro-1-(methylsulfanyl)benzene (0.5 g, 2.26 mmol) was added dropwise to a suspension of activated Mg turnings (1.92 g, 79 mmol) under N2(g) in dry THF (80 ml.) and the reaction warmed until Grignard formation had initiated. The remaining 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (17 g, 76.89 mmol) was added dropwise, so as to maintain the temperature below 50°C and after complete addition, the reaction was allowed to cool to rt and stirred for 16 hrs. The solution was added via cannula to an ice- cooled solution of iodine (24.11 g, 94.99 mmol) in dry THF (80 mL) maintaining the temperature below 10 °C. The reaction was stirred at 0 °C for 1 hr, at rt for 1 hr then poured into an ice-cold sat. NH4CI soln. (300 mL). The mixture was concentrated in vacuo to remove organic solvents then extracted with Et20 (3 x 300 mL). The combined organic layers were washed with a sat. Na2S203 soln., dried (Na2S04), and concentrated in vacuo to afford the title compound as a brown oil, 21.5 g, 83 %. 1 H NMR (CDCIs, 396 MHz): 5 2.45 (s, 3H), 7.08-7.11 (m, 2H), 7.55 (dd, 1 H).
83% Stage #1: 2-bromo-4-fluoro-1-(methylsulfanyl)benzene With magnesium In tetrahydrofuran at 20 - 50℃; for 16h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 2h; 4-Fluoro-2-iodo-1-(methylsulfanyr) benzene 2-Bromo-4-fluoro-1-(methylsulfanyl)benzene (0.5 g, 2.26 mmol) was added dropwise to a suspension of activated Mg turnings (1.92 g, 79 mmol) under N2 in dry THF (80 ml) and the reaction warmed until Grignard formation had initiated. The remaining 2-bromo-4- fluoro-1-(methylsulfanyl)benzene (17 g, 76.89 mmol) was added dropwise, so as to maintain the temperature below 50°C and after complete addition, the reaction was allowed to cool to rt and stirred for 16 h. The solution was added via cannula to an ice- cooled solution of iodine (24.11 g, 94.99 mmol) in dry THF (80 ml) maintaining the temperature below 10 °C. The reaction was stirred at 0°C for 1 h, at rt for 1 h, then poured into an ice-cold sat. NH4CI soln. (300 ml). The mixture was concentrated in vacuo to remove organic solvents then extracted with Et20 (3 x 300 ml). The combined organic layers were washed with a sat. Na2S203 solution, dried (Na2S04), and concentrated in vacuo to afford the title compound as a brown oil (21.5 g, 83%). 1 H NMR (CDCI3, 396 MHz): d: 7.55 (m, 1 H), 7.08-7.11 (m, 2H), 2.45 (s, 3H).
83% Stage #1: 2-bromo-4-fluoro-1-(methylsulfanyl)benzene With magnesium In tetrahydrofuran at 20 - 50℃; for 16h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; 1 4-fluoro-2-iodo-1-(methylsulfanyl)benzene 2-Bromo-4-fluoro-1-(methylsulfanyl)benzene (0.5 g, 2.26 mmol) was added dropwise to a suspension of activated Mg turnings (1.92 g, 79 mmol) under N2(g) in dry THF (80 mL) and the reaction warmed until Grignard formation had initiated. The remaining 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (17 g, 76.89 mmol) was added dropwise, so as to maintain the temperature below 50°C and after complete addition, the reaction was allowed to cool to rt and stirred for 16 hrs. The solution was added via cannula to an ice- cooled solution of iodine (24.11 g, 94.99 mmol) in dry THF (80 mL) maintaining the temperature below 10 °C. The reaction was stirred at 0 °C for 1 hr, at rt for 1 hr then poured into an ice-cold sat. NH4CI soln. (300 mL). The mixture was concentrated in vacuo to remove organic solvents then extracted with Et20 (3 x 300 mL). The combined organic layers were washed with a sat. Na2S203 soln., dried (Na2S04), and concentrated in vacuo to afford the title compound as a brown oil, 21.5 g, 83 %. 1H NMR (CDCb, 396 MHz): <52.45 (s, 3H), 7.08-7.11 (m, 2H), 7.55 (dd, 1 H).
83% Stage #1: 2-bromo-4-fluoro-1-(methylsulfanyl)benzene With magnesium In tetrahydrofuran at 20 - 50℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 2h; 20 4-Fluoro-2-iodo-1-(methylsulfanyl)benzene 2-Bromo-4-fluoro-1-(methylsulfanyl)benzene (0.5 g, 2.26 mmol) was added dropwise to a suspension of activated Mg turnings (1.92 g, 79 mmol) under N2 in dry THF (80 ml) and the reaction warmed until Grignard formation had initiated. The remaining 2-bromo-4- fluoro-1-(methylsulfanyl)benzene (17 g, 76.89 mmol) was added dropwise, so as to maintain the temperature below 50°C and after complete addition, the reaction was allowed to cool to rt and stirred for 16 h. The solution was added via cannula to an ice- cooled solution of iodine (24.11 g, 94.99 mmol) in dry THF (80 ml) maintaining the temperature below 10 °C. The reaction was stirred at 0°C for 1 h, at rt for 1 h, then poured into an ice-cold sat. NH4CI soln. (300 ml). The mixture was concentrated in vacuo to remove organic solvents then extracted with Et22O (3 x 300 ml). The combined organic layers were washed with a sat. Na2S2C>3 solution, dried (Na2SO4), and concentrated in vacuo to afford the title compound as a brown oil (21.5 g, 83%). 1H NMR (CDCb, 396 MHz): d: 7.55 (m, 1H), 7.08-7.11 (m, 2H), 2.45 (s, 3H).

  • 4
  • [ 91524-70-8 ]
  • tert-butyl (2R,4S)-4-fluoro-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4-di-tert-butyl-2,2-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere
  • 5
  • [ 91524-70-8 ]
  • (R)-N-[(1Z)-[5-fluoro-2-(methylsulfanyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2: caesium carbonate / dichloromethane / 18 h / 20 °C
Multi-step reaction with 2 steps 1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2: caesium carbonate / dichloromethane / 18 h / 20 °C
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2: caesium carbonate / dichloromethane / 18 h / 20 °C
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere 1.2: 0.5 h / -78 °C 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C

  • 6
  • [ 91524-70-8 ]
  • (R)-N-((1R)-3-(1<SUB>,</SUB>3-dioxan-2-yl)-1-(5-fluoro-2-(methylsulfanyl)phenyl)propyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: -50 - 20 °C
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere 1.2: 0.5 h / -78 °C 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 °C

  • 7
  • [ 91524-70-8 ]
  • (2R)-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 16 h / 20 °C 4.2: 16 h / 20 °C
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: -50 - 20 °C 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere 1.2: 0.5 h / -78 °C 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 °C 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C

  • 8
  • [ 91524-70-8 ]
  • (2R,4S)-4-fluoro-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4-di-tert-butyl-2,2-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water; 1,4-dioxane / 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C

  • 9
  • [ 91524-70-8 ]
  • ethyl 6-[(2R)-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 16 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C
Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: -50 - 20 °C 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / water; 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C
Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere 1.2: 0.5 h / -78 °C 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 °C 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C

  • 10
  • [ 91524-70-8 ]
  • 6-[(2R)-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 16 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: water; potassium hydroxide / ethanol / 1.5 h / 20 °C
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: -50 - 20 °C 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / water; 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: water; potassium hydroxide / ethanol / 1.5 h / 20 °C
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: potassium hydroxide; water / ethanol / 1.5 h / 20 °C
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere 1.2: 0.5 h / -78 °C 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 °C 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: potassium hydroxide / ethanol; water / 1.5 h / 20 °C

  • 11
  • [ 91524-70-8 ]
  • 6-[(2R)-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]-N-[(3R)-oxan-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 16 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: water; potassium hydroxide / ethanol / 1.5 h / 20 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 0.08 h / 20 °C 7.2: 16 h / 2 °C
Multi-step reaction with 7 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: potassium hydroxide; water / ethanol / 1.5 h / 20 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C 7.2: 16 h / 20 °C
  • 12
  • [ 91524-70-8 ]
  • 6-[(2R)-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]-N-[(3R)-oxan-3-yl]imidazo[1,2-b]pyridazine-3-carbothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 16 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: water; potassium hydroxide / ethanol / 1.5 h / 20 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 0.08 h / 20 °C 7.2: 16 h / 2 °C 8.1: Lawessons reagent / toluene / 16 h / 100 °C
Multi-step reaction with 8 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: potassium hydroxide; water / ethanol / 1.5 h / 20 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C 7.2: 16 h / 20 °C 8.1: Lawessons reagent / toluene / 16 h / 100 °C
  • 13
  • [ 91524-70-8 ]
  • (Z)-N'-cyano-6-[(2R)-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]-N-[(3R)-oxan-3-yl]imidazo[1,2-b]pyridazine-3-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 16 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: water; potassium hydroxide / ethanol / 1.5 h / 20 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 0.08 h / 20 °C 7.2: 16 h / 2 °C 8.1: Lawessons reagent / toluene / 16 h / 100 °C 9.1: mercury dichloride / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere 2.1: caesium carbonate / dichloromethane / 18 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere 3.2: 1 h / -50 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / water / 0.5 h / 20 °C 4.2: 16 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 5.2: 16 h / 130 °C 6.1: potassium hydroxide; water / ethanol / 1.5 h / 20 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C 7.2: 16 h / 20 °C 8.1: Lawessons reagent / toluene / 16 h / 100 °C 9.1: mercury dichloride / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
  • 14
  • [ 91524-70-8 ]
  • [ 33513-42-7 ]
  • [ 160503-79-7 ]
YieldReaction ConditionsOperation in experiment
52% With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; 5-fluoro-2-(methylsulfanyl)benzaldehyde n-BuLi in hexane (2.5 M, 0.4 mL, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 mL) at -78 °C under N2(g), so the temperature was maintained below -70 °C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH4CI soln. (10 mL), warmed to rt and extracted with EtOAc (10 mL). The organic extracts were washed with saturated brine (10 mL), dried (MgS0 ), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes: EtOAc (95:5) to afford the title compound as colourless oil, 88 mg, 52%. 1 H NMR (CDCIs, 400MHz): d_2.51 (s, 3H), 7.25-7.30 (m, 1 H), 7.35-7.39 (m, 1 H), 7.52- 7.56 (m, 1 H), 10.35 (s, 1 H).
52% With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; 5-Fluoro-2-(methylsulfanyl)benzaldehyde n-BuLi in hexane (2.5 M, 0.4 ml, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 ml) at -78°C under N2 atmosphere, so the temperature was maintained below -70°C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH4CI solution (10 ml), warmed to rt and extracted with EtOAc (10 ml). The organic extracts were washed with saturated brine (10 ml), dried (MgS04), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes: EtOAc (95:5) to afford the title compound as colourless oil (88 mg, 52%). 1 H NMR (CDCIs, 400MHz): d: 10.35 (s, 1 H); 7.52-7.56 (m, 1 H); 7.35-7.39 (m, 1 H), 7.25- 7.30 (m, 1 H); 2.51 (s, 3H).
52% With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; 7 5-fluoro-2-(methylsulfanyl)benzaldehyde n-BuLi in hexane (2.5 M, 0.4 ml_, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 mL) at -78 °C under N2(g), so the temperature was maintained below -70 °C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH CI soln. (10 ml_), warmed to rt and extracted with EtOAc (10 ml_). The organic extracts were washed with saturated brine (10 ml_), dried (MgS04), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes:EtOAc (95:5) to afford the title compound as colourless oil, 88 mg, 52%. 1H NMR (CDC , 400MHz): d_2.51 (s, 3H), 7.25-7.30 (m, 1H), 7.35-7.39 (m, 1H), 7.52- 7.56 (m, 1 H), 10.35 (s, 1 H).
52% Stage #1: 2-bromo-4-fluoro-1-(methylsulfanyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 0.5h; 1 5-Fluoro-2-(methylsulfanyl)benzaldehyde n-BuLi in hexane (2.5 M, 0.4 ml, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 ml) at -78°C under N2 atmosphere, so the temperature was maintained below -70°C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH4CI solution (10 ml), warmed to rt and extracted with EtOAc (10 ml). The organic extracts were washed with saturated brine (10 ml), dried (MgSO4), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes: EtOAc (95:5) to afford the title compound as colourless oil (88 mg, 52%). (0330) 1H NMR (CDCl3, 400MHz): d: 10.35 (s, 1H); 7.52-7.56 (m, 1H); 7.35-7.39 (m, 1H), 7.25- 7.30 (m, 1H); 2.51 (s, 3H).

  • 15
  • [ 91524-70-8 ]
  • 6-[(2R,4S)-4-fluoro-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]-N-[(3S)-1-[(3-hydroxyphenyl)methyl]pyrrolidin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4-di-tert-butyl-2,2-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water; 1,4-dioxane / 2 h / 20 °C 4.1: potassium fluoride / dimethyl sulfoxide / 20 h / 130 °C 5.1: water; potassium hydroxide / ethanol / 0.25 h / 20 °C 6.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.5 h / 20 - 21 °C 7.1: triethylamine / dichloromethane / 3.67 h / 3 - 20 °C
Multi-step reaction with 7 steps 1.1: magnesium / tetrahydrofuran / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C 4.1: potassium fluoride / dimethyl sulfoxide / 20 h / 130 °C 5.1: potassium hydroxide / ethanol; water / 0.25 h / 20 °C 6.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 7.1: triethylamine / dichloromethane / 3.7 h / 3 - 20 °C
  • 16
  • [ 91524-70-8 ]
  • C32H27F4N5O3S [ No CAS ]
  • 6-[(2R,4S)-4-fluoro-2-[5-fluoro-2-(methylsulfanyl)phenyl]pyrrolidin-1-yl]-N-[(4-fluoro-3-hydroxyphenyl)methyl]imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: magnesium / tetrahydrofuran / 16 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C 2.1: nickel(II) bromide dimethoxyethane; 4,4-di-tert-butyl-2,2-bipyridine; zinc / N,N-dimethyl acetamide / 17 h / 28 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water; 1,4-dioxane / 2 h / 20 °C 4.1: potassium fluoride / dimethyl sulfoxide / 20 h / 130 °C 5.1: water; potassium hydroxide / ethanol / 0.25 h / 20 °C 6.1: O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 1.5 h / 20 °C
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