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Product Details of [ 949159-95-9 ]

CAS No. :949159-95-9 MDL No. :MFCD12545938
Formula : C8H7FO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WZADRGNQKQFMHI-UHFFFAOYSA-N
M.W : 154.14 Pubchem ID :45119097
Synonyms :

Safety of [ 949159-95-9 ]

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 [ 949159-95-9 ]

* 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 [ 949159-95-9 ]

[ 949159-95-9 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 369-33-5 ]
  • [ 949159-95-9 ]
  • 2
  • [ 949159-95-9 ]
  • [ 74-88-4 ]
  • [ 64287-19-0 ]
YieldReaction ConditionsOperation in experiment
92% With sodium carbonate In N,N-dimethyl-formamide at 90℃; 4.4 Step 4. Into a 50 mL round bottom flask was added l-(4-fluoro-3- hydroxyphenyl)ethanone (2.7 g, 17.53 mmol), DMF (30 mL), sodium carbonate (5 g, 47.17 mmol), and iodomethane (5 g, 35.21 mmol). The solution was stirred overnight at 90 0C. The reaction progress was monitored by TLC (EtO Ac/P (1 :1, v/v)). The mixture was concentrated by evaporation under vacuum using a rotary evaporator and the residue was dissolved in 100 mL of DCM and 100 mL of H2O. The organic phase was separated and washed with H2O, dried over anhydrous Na2SO^ and concentrated by evaporation under vacuum using a rotary evaporator to provide 2.9 g (92%) of l-(4-fluoro-3- methoxyphenyl)ethanone as a light yellow solid.
  • 3
  • [ 2002-82-6 ]
  • [ 949159-95-9 ]
YieldReaction ConditionsOperation in experiment
19% Stage #1: 1-(3-amino-4-fluorophenyl)ethanone With sulfuric acid; sodium nitrite In water at 0 - 5℃; Stage #2: With copper(I) oxide; sulfuric acid; water; copper(II) nitrate at 20℃; for 0.25h; 4.3 Step 3. Into a 2L 3-necked round bottom flask was added l-(3-amino-4- fiuorophenyl)ethanone (13.6 g, 88.89 mmol), 230 mL of 35% sulfuric acid in water, and 160 mL OfH2O. This was followed by the dropwise addition of a solution of sodium nitrate (6.2 g, 89.86 mmol) in water (30 mL) with stirring, while maintaining the temperature between -5 and 0 0C. This was followed by the addition of a solution of cupric nitrate (300 g, 1.24 mol) in water (800 mL) and then cuprous oxide (30 g, 209.79 mmol). The resulting solution was stirred at room temperature for 15 min and the reaction progress was monitored by TLC (EtOAc/PE (1 :1, v/v)). The reaction mixture was filtered and the filtrate was extracted with DCM. The combined organic layers were dried (anhydrous Na2SO4) and concentrated (rotary evaporator). The residue was purified by silica gel chromatography using a gradient elution of petroleum ether/EtOAc going from 30:1 (v/v) to 10:1 (v/v) to provide 2.6 g (19 %) of l-(4-fluoro-3-hydroxyphenyl)ethanone as a pale yellow solid.
  • 4
  • [ 64287-19-0 ]
  • [ 949159-95-9 ]
YieldReaction ConditionsOperation in experiment
14% With water; hydrogen bromide for 16h; Heating / reflux; VIII 4-Fluoro-3 -hvdroxyacetophenone; A suspension of 4-fluoro-3-methoxyacetophenone (0.316 g, 1.88 mmol) in 48% hydrobromic acid (10 ml) was stirred at reflux under nitrogen for 16h. After cooling to room temperature, the suspension was poured over crushed ice and extracted with dichloromethane (x3). The combined organic extracts were washed with water (x2), dried over magnesium sulphate, filtered and concentrated to an orange oil. The crude product was purified by column chromatography (SiO2), eluting with 9:1 petrol/ethyl acetate to give a 4-fluoro-3-hydroxyacetophenone as an orange solid (0.041 g, 14.0%).Rf- 0.33 (7:3 petrol/ethyl acetate).1H nmr (CDCl3): δ2.57 (s, 3H); 5.35 (d, J 4.0 Hz, IH); 7.15 (dd, J 10.0, 8.3 Hz, IH); 7.30 (ddd, J8.4, 4.7, 2.1 Hz, IH); 7.63 (dd, J8.5, 2.1 Hz, IH).MS ESI +ve: M++H, 155.0.MS ESI -ve: M+-H, 152.9.
  • 5
  • [ 1056479-02-7 ]
  • [ 949159-95-9 ]
  • [ 1072710-27-0 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine In ethanol for 4h; Heating / reflux; VIII 4'-Fluoro-3'-hydroxyacetophenone-O-[(benzo[c][l,2,5]oxadiazol-5-yl)methyl]oxime (CP9-135); A solution of 4-fluoro-3-hydroxyacetophenone (0.041 g, 0.263 mmol), (benzo[c][l,2,5]oxadiazol-5-yl)methoxyamine hydrochloride (0.047 g, 0.232 mmol) and pyridine (0.09 ml, 1.11 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 4h and cooled to room temperature. The solution was concentrated to a yellow oil which was diluted with water/dichloromethane. The resultant mixture was extracted with dichloromethane (x3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to a pale yellow solid. The crude product was purified by column chromatography (SiO2), eluting with 8:2 petrol/ethyl acetate, to give 3'-fluoro-4'-hydroxyacetophenone-O-[(benzo[c][l,2,5]oxadiazol-5- yl)methyl]oxime (CP9-135) as a light orange solid (0.050 g, 72%), m.p. 125-126°.Rf ~ 0.61 (7:3 petrol/ethyl acetate).1H nmr (CDCl3): 52.29 (s, 3H); 5.19 (d, J4.0 Hz, IH); 5.29 (d, J 1.0 Hz, IH); 7.05 (dd, J 10.5, 9.4 Hz, IH); 7.13 (ddd, J9.4, 7.0, 2.1 Hz, IH); 7.31 (dd, J8.5, 2.1 Hz, IH); 7.43 (dd, J9.4, 1.1 Hz, IH); 7.78 (apparent pentet, J 1.2 Hz, IH); 7.82 (dd, J9.5, 1.0 Hz, IH).MS ESI +ve: M++H, 302.2.MS ESI -ve: M+-H, 300.1.
  • 6
  • [ 553-90-2 ]
  • [ 949159-95-9 ]
  • methyl 4-(4-fluoro-3-hydroxyphenyl)-2,4-dioxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With sodium methylate In ethanol at 20℃; for 24h;
  • 7
  • [ 75-16-1 ]
  • [ 949159-95-9 ]
  • 2-fluoro-5-(2-hydroxypropan-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.88 g In tetrahydrofuran at 10 - 35℃; for 1h; Inert atmosphere; 137 Reference Example 137 2-fluoro-5-(2-hydroxypropan-2-yl)phenol To a solution of 1-(4-fluoro-3-hydroxyphenyl)ethanone (0.92 g) in THF (10 mL) was added 1 mol/L methylmagnesium bromide (THF solution) (18 mL) at 0°C, and the mixture was stirred under a nitrogen atmosphere at room temperature for 1 hr. The reaction solution was neutralized with 1N hydrochloric acid, and ethyl acetate was added. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (0.88 g). 1H NMR (300 MHz, DMSO-d6) δ 1.37 (6H, s), 4.93 (1H, s), 6.73-6.88 (1H, m), 6.94-7.17 (2H, m), 9.59 (1H, s).
  • 8
  • [ 553-90-2 ]
  • [ 949159-95-9 ]
  • methyl 4-(4-fluoro-3-hydroxyphenyl)-2,4-dioxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With sodium methylate In diethyl ether at 20℃; for 24h; Methyl 4-(4-fluoro-3-hydroxyphenyl)-2,4-dioxobutanoate (KSC-392-097): To a solution of l-(4-fluoro-3-hydroxyphenyl)ethanone (0.120 g, 0.779 mmol) in Et20 (3 ml, 0.25M) was added sodium methoxide (0.267 ml, 1.168 mmol), followed by dimethyl oxalate (0.092 g, 0.779 mmol) and the mixture was stirred for 24h at room temperature. Upon completion, the mixture was quenched with IN HC1 and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and evaporated to dryness. The resulting residue was purified MPLC (silica, 10-100% hexanes/EtOAc) to provide methyl 4-(4-fiuoro-3-hydroxyphenyl)-2,4-dioxobutanoate (0.133 g, 0.554 mmol, 71 % yield) (KSC-392-097) as light yellow liquid which solidified on cooling. 1H NMR (400 MHz, Acetone-d6) δ 7.72 (dd, J= 8.5, 2.3 Hz, 1H), 7.66 (ddd, J= 8.6, 4.4, 2.3 Hz, 1H), 7.31 (dd, J = 10.7, 8.5 Hz, 1H), 7.08 (s, 1H), 3.90 (s, 3H); HRMS (ESI-TOF) m/z: [M + H]+ Calcd for Ci4HioC103 261.0324; Found 261.0348.
  • 9
  • [ 65865-28-3 ]
  • [ 949159-95-9 ]
  • 1-(4-fluoro-3-((5-(trifluoromethyl)furan-2-yl)methoxy)phenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h; 125.1 1 -(4-fluoro-3 -((5 -(trifluoromethyl)furan-2-yl)methoxy)phenyl)ethan- 1-one. [0448] A solution of di-t-butyl diazocarboxylate (480 mg, 2 mmol) in THF (11 mL) was cooled to 0°C and triphenyl phosphine (553 mg, 2 mmol) was added. (5- (Trifluoromethyl)furan-2-yl)methanol (350 mg, 2 mmol) and 3-hydroxy-4- fluoroacetophenone (250 mg, 1.6 mmol) were sequentially added and the cooling was removed. The reaction mixture was stirred for 30 mm, concentrated by rotary evaporator and purified by flash chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-30% gradient) to give 1 -(4-fluoro-3 -((5-(trifluoromethyl)furan-2-yl)methoxy)phenyl)ethan- 1-one (0.66 g, 95%).
95% With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h; Step 1: 1-(4-fluoro-3-((5-(trifluoromethyl)furan-2-yl)methoxy)phenyl)ethan-1-one. A solution of di-t-butyl diazocarboxylate (480 mg, 2 mmol) in THF (11 mL) was cooled to 0 oC andtriphenyl phosphine (553 mg, 2 mmol) was added. (5-(trifluoromethyl)furan-2-yl)methanol (350 mg, 2mmol) and 3-hydroxy-4-fluoroacetophenone (250 mg, 1.6 mmol) were sequentially added and thecooling was removed. The reaction mixture was stirred for 30 min, concentrated by rotary evaporatorand purified by flash chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-30% gradient) to give 1-(4-fluoro-3-((5-(trifluoromethyl)furan-2-yl)methoxy)phenyl)ethan-1-one (0.66 g, 95%). LCMS RT = 1.10min; MS (ESI) m/z = 303.0 [M+H]+.
  • 10
  • [ 7051-34-5 ]
  • [ 949159-95-9 ]
  • 1-(3-(cyclopropylmethoxy)-4-fluorophenyl)ethane-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 76a.1 10669] Step 1: Synthesis of i-(3(cydopropyniethoxy)-4-41uorophenyI) ethaii-4-one (3-I) To a stirred solution of 1i (5.0 g, 32A mmoi) in DMF (50 mL) was added K2C03 (ii .2 g, 1 .1 rnmol) followed by addition of (brornomethyi)cyclopropane (3.73 g, 3 .9rnmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-1 (6.61 g, crude), LCMS: 2O.95 (M-f 1).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 76a.1 Step 1: Synthesis of l-(3-(cyclopropylmethoxy)-4-fluorophenyl) ethan-l-one (3- 1) To a stirred solution of 1-1 (5.0 g, 32.4 mmol) in DMF (50 mL) was added K2CO3(11.2 g, 81.1 mmol) followed by addition of (bromomethyl)cyclopropane (3.73 g, 38.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtO Ac. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-1 (6.61 g, crude). LCMS: 208.95 (M+l).
With potassium carbonate In acetonitrile for 2h; Reflux; 76a.1 Step 1: Synthesis of 1-(3-(cyclopropylmethoxy)-4-fluorophenyl) ethan- 1-one (3-1) To a stirred solution of 1-1 (5.0 g, 32.4 mmol) in DMF (50 mL) was added K2C03 (11.2 g, 81.1 mmol) followed by addition of (bromomethyl)cyclopropane (3.73 g, 38.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-1 (6.61 g, crude). LCMS: 208.95 (M+1).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 76a.1 Step 1: Synthesis of l-(3-(cyclopropylmethoxy)-4-fluorophenyl) ethan-l-one (3- 1) To a stirred solution of 1-1 (5.0 g, 32.4 mmol) in DMF (50 mL) was added K2CO3 (11.2 g, 81.1 mmol) followed by addition of (bromomethyl)cyclopropane (3.73 g, 38.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-1 (6.61 g, crude). LCMS: 208.95 (M+l).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 76a.1 Step 1: Synthesis of 1-(3-(cyclopropylmethoxy)-4-fluorophenyl) ethan-1-one (3- To a stirred solution of 1-1 (5.0 g, 32.4 mmol) in DMF (50 mL) was added K2C03 (11.2 g, 81.1 mmol) followed by addition of (bromomethyl)cyclopropane (3.73 g, 38.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-1 (6.61 g, crude). LCMS: 208.95 (M+1).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 76a.1 Production Example 76a: Synthesis of N-(1-(3-(2-cyclopropylethoxy)-4-fluorophenyl) ethyl)-5-(2, 4-dioxoimidazolidin-1-yl) pentane-1-sulfonamide Scheme 13. [0717] Step 1: Synthesis of 1-(3-(cyclopropylmethoxy)-4-fluorophenyl) ethan-1-one (3- l) To a stirred solution of 1-l (5.0 g, 32.4 mmol) in DMF (50 mL) was added K2CO3 (11.2 g, 81.1 mmol) followed by addition of (bromomethyl)cyclopropane (3.73 g, 38.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-l (6.61 g, crude). LCMS: 208.95 (M+1).

  • 11
  • [ 949159-95-9 ]
  • (S)-N-(1-(4-fluoro-3-propoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C
  • 12
  • [ 949159-95-9 ]
  • (S)-N-((S)-1-(4-fluoro-3-propoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C
  • 13
  • [ 949159-95-9 ]
  • (S)-1-(4-fluoro-3-propoxyphenyl)ethan-1-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C
  • 14
  • [ 949159-95-9 ]
  • (S)-5-(1,3-dioxoisoindolin-2-yl)-N-(1-(4-fluoro-3-propoxyphenyl)ethyl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: methanol; hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.4 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3 h / 0 °C

  • 15
  • [ 949159-95-9 ]
  • (S)-5-amino-N-(1-(4-fluoro-3-propoxyphenyl)ethyl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: methanol; hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.4 h / 0 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3 h / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice

  • 16
  • [ 949159-95-9 ]
  • ethyl (S)-(5-(N-(1-(4-fluoro-3-propoxyphenyl)ethyl)sulfamoyl)pentyl)glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: methanol; hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: toluene; methanol / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.4 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: methanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: methanol; toluene / 1 h / 20 °C 7.2: 20 °C
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3 h / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice 7: sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid / methanol; ethanol; toluene / 20 °C

  • 17
  • [ 949159-95-9 ]
  • (S)-5-(2,4-dioxoimidazolidin-1-yl)-N-(1-(4-fluoro-3-propoxyphenyl)ethyl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: methanol; hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: toluene; methanol / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.4 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: methanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: methanol; toluene / 1 h / 20 °C 7.2: 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3 h / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice 7: sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid / methanol; ethanol; toluene / 20 °C 8: acetic acid / 20 - 60 °C

  • 18
  • [ 949159-95-9 ]
  • (S)-N-(1-(3-(allyloxy)-4-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C
  • 19
  • [ 949159-95-9 ]
  • (S)-N-((S)-1-(3-(allyloxy)-4-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C
  • 20
  • [ 949159-95-9 ]
  • (S)-N-(1-(3-(allyloxy)-4-fluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.4 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 0 °C

  • 21
  • [ 949159-95-9 ]
  • (S)-5-amino-N-(1-(3-(cyclopropylmethoxy)-4-fluorophenyl)ethyl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.4 h / 0 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice

  • 22
  • [ 949159-95-9 ]
  • ethyl (S)-(5-(N-(1-(3-(allyloxy)-4-fluorophenyl)ethyl)sulfamoyl)pentyl)glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.4 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 20 °C
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice 7: sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid / ethanol; toluene / 20 °C

  • 23
  • [ 949159-95-9 ]
  • (S)-N-(1-(3-(allyloxy)-4-fluorophenyl)ethyl)-5-(2,4-dioxoimidazolidin-1-yl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.4 h / 0 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 - 20 °C 5.2: 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice 7: sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid / ethanol; toluene / 20 °C 8: acetic acid / 20 - 60 °C

  • 24
  • [ 949159-95-9 ]
  • (S)-N-(1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C
  • 25
  • [ 949159-95-9 ]
  • (S)-N-((S)-1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C 3: diisobutylaluminium hydride / toluene / -78 °C
  • 26
  • [ 949159-95-9 ]
  • (S)-1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-1-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C 3: diisobutylaluminium hydride / toluene / -78 °C 4: hydrogenchloride / 1,4-dioxane / 20 °C

  • 27
  • [ 949159-95-9 ]
  • (S)-N-(1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.4 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 °C 5.2: 3.42 h / 0 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C 3: diisobutylaluminium hydride / toluene / -78 °C 4: hydrogenchloride / 1,4-dioxane / 20 °C 5: triethylamine / dichloromethane / 0 °C

  • 28
  • [ 949159-95-9 ]
  • (S)-5-amino-N-(1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethyl)pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 °C 6: hydrazine hydrate / methanol / 3 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.4 h / 0 °C 6: hydrazine hydrate / methanol / 3 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6: hydrazine hydrate / methanol / 8 h / 0 - 20 °C
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 °C 5.2: 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C 3: diisobutylaluminium hydride / toluene / -78 °C 4: hydrogenchloride / 1,4-dioxane / 20 °C 5: triethylamine / dichloromethane / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice

  • 29
  • [ 949159-95-9 ]
  • ethyl (S)-(5-(N-(1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethyl)sulfamoyl)pentyl)glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.4 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 °C 5.2: 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C 3: diisobutylaluminium hydride / toluene / -78 °C 4: hydrogenchloride / 1,4-dioxane / 20 °C 5: triethylamine / dichloromethane / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice 7: sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid / ethanol; toluene / 20 °C

  • 30
  • [ 949159-95-9 ]
  • (S)-N-(1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethyl)-5-(2,4-dioxoimidazolidin-1-yl) pentane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.4 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 3.42 h / 0 - 20 °C 6.1: hydrazine hydrate / methanol / 8 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2.1: titanium(IV) isopropylate / toluene / 16 h / 90 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 4.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0 °C 5.2: 3.42 h / 0 °C 6.1: hydrazine hydrate / methanol / 3 h / 0 - 20 °C 7.1: ethanol; toluene / 1 h / 20 °C 7.2: 4.17 h / 20 °C 8.1: acetic acid / 22 h / 20 - 60 °C
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: titanium(IV) isopropylate / toluene / 90 °C 3: diisobutylaluminium hydride / toluene / -78 °C 4: hydrogenchloride / 1,4-dioxane / 20 °C 5: triethylamine / dichloromethane / 0 °C 6: hydrazine hydrate / methanol / 0 - 20 °C / Cooling with ice 7: sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid / ethanol; toluene / 20 °C 8: acetic acid / 20 - 60 °C

  • 31
  • [ 106-94-5 ]
  • [ 949159-95-9 ]
  • 1-(4-fluoro-3-propoxyphenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux; 71a.1 [0617] Step 1: Synthesis of 1(441uoro-3-propoxyphenyl) ethan4one (3-f) To a stirred solution of 14(3.0 g, 19.4 mmoi) inDMF (50 mL) was added K2C03 (8.0 g, 58.4 rnmol) followed by addition of 1-bromopropane 124) (4.75 g, 38.9 rnmol) and the reaction mixture was refiuxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layerwas washed with brine, dried over anhydrous Na2SO,, and concentrated under reduced pressure Lo afford 3 (4.0g. crude).‘H NMR (400 MFIz, DMSOd6) 7,65-7,57 (in, 1H), 7.52-7.48 (ni, 11-1), 7.12 (t.J= 53 Flz, IH), 4M6-4M3 (in, 2H), 2.66 (5, 3H), 1.921.82 (m, 2H).1,07-1,04 (in, 3H).
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux; 71a.1 Step 1: Synthesis of l-(4-fluoro-3-propoxyphenyl) ethan-l-one (3-f) To a stirred solution of 1-f (3.0 g, 19.4 mmol) in DMF (50 mL) was added K2CO3(8.0 g, 58.4 mmol) followed by addition of 1-bromopropane (2-f) (4.75 g, 38.9 mmol) and the reaction mixture was refluxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04and concentrated under reduced pressure to afford 3-f (4.0 g, crude).1H MR (400 MHz, DMSO-d6) δ 7.65-7.57 (m, 1H), 7.52-7.48 (m, 1H), 7.12 (t, J = 53 Hz, 1H), 4.06-4.03 (m, 2H), 2.66 (s, 3H), 1.92-1.82 (m, 2H).1.07-1.04 (m, 3H).
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux; 71a.1 Step 1: Synthesis of 1-(4-fluoro-3-propoxyphenyl) ethan-1-one (3-f) To a stirred solution of 1-f(3.0 g, 19.4 mmol) in DMF (50 mL) was added K2C03 (8.0 g, 58.4 mmol) followed by addition of 1-bromopropane (2-f) (4.75 g, 38.9 mmol) and the reaction mixture was refluxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-f (4.0 g, crude). ‘H NMR (400 MFIz, DMSO-d6) 7.65-7.57 (m, 1H), 7.52-7.48 (m, 1H), 7.12 (t, J= 53 Hz, 1H), 4.06-4.03 (m, 2H), 2.66 (s, 3H), 1.92-1.82 (m, 2H).1.07-1.04 (m, 3H).
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux; 71a.1 Synthesis of l-(4-fluoro-3-propoxyphenyl) ethan-l-one (3-f) To a stirred solution of 1-f (3.0 g, 19.4 mmol) in DMF (50 mL) was added K2CO3 (8.0 g, 58.4 mmol) followed by addition of 1-bromopropane (2-f) (4.75 g, 38.9 mmol) and the reaction mixture was refluxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 3-f (4.0 g, crude). 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.57 (m, 1H), 7.52-7.48 (m, 1H), 7.12 (t, J= 53 Hz, 1H), 4.06-4.03 (m, 2H), 2.66 (s, 3H), 1.92-1.82 (m, 2H).1.07-1.04 (m, 3H).
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux; 71a.1 Step 1: Synthesis of 1-(4-fluoro-3-propoxyphenyl) ethan-1-one (3-f) To a stirred solution of 1-f(3.0 g, 19.4 mmol) in DMF (50 mL) was added K2C03 (8.0 g, 58.4 mmol) followed by addition of 1-bromopropane (2-f) (4.75 g, 38.9 mmol) and the reaction mixture was refluxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-f (4.0 g, crude).‘HNMR (400 MFIz, DMSO-d6) 7.65-7.57 (m, 1H), 7.52-7.48 (m, 1H), 7.12 (t, J 53 Hz, 1H), 4.06-4.03 (m, 2H), 2.66 (s, 3H), 1.92-1.82 (m, 2H).1.07-1.04 (m, 3H).
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux; 71a.1 Production Example 71a: Synthesis of (S)-5-(2,4-dioxoimidazolidin-1-yl)-N-(1-(4- fluoro-3-propoxyphenyl) ethyl) pentane-1-sulfonamide h m [0665] Step 1: Synthesis of 1-(4-fluoro-3-propoxyphenyl) ethan-1-one (3-f) To a stirred solution of 1-f (3.0 g, 19.4 mmol) in DMF (50 mL) was added K2CO3 (8.0 g, 58.4 mmol) followed by addition of 1-bromopropane (2-f) (4.75 g, 38.9 mmol) and the reaction mixture was refluxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-f (4.0 g, crude). 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.57 (m, 1H), 7.52-7.48 (m, 1H), 7.12 (t, J = 53 Hz, 1H), 4.06-4.03 (m, 2H), 2.66 (s, 3H), 1.92-1.82 (m, 2H).1.07-1.04 (m, 3H).

  • 32
  • [ 106-95-6 ]
  • [ 949159-95-9 ]
  • 1-(3-(allyloxy)-4-fluorophenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 72a.1 [0625] Step 1: Synthesis of F-(3(aIIy1oxy)4Iuoropheny1)ethan4one (3g) To a stirred solution of 1.g (2.0 g, 12,9 rnmoi) in DMF (10 mL) was added K2C03 (5,37 g, 38.9 mmol) followed by addition of 3bromoprop-1ene (3g’) (3.14 g, 25.9 mmol) and the reaction mixture was refiuxed for 2 ii (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-g (1.8g, crude). LCMS: 195.05 (M-F-1).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 72a.1 Step 1: Synthesis of l-(3-(allyloxy)-4-fluorophenyl)ethan-l-one (3-g) To a stirred solution of 1-g (2.0 g, 12.9 mmol) in DMF (10 mL) was added K2CO3(5.37 g, 38.9 mmol) followed by addition of 3-bromoprop-l-ene (3-g) (3.14 g, 25.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtO Ac. The combined organic layer was washed with brine, dried over anhydrous Na2S04and concentrated under reduced pressure to afford 3-g (1.8 g, crude). LCMS: 195.05 (M+l).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 72a.1 Step 1: Synthesis of 1-(3-(allyloxy)-4-fluorophenyl)ethan- 1-one (3-g) To a stirred solution of 1-g (2.0 g, 12.9 mmol) in DMF (10 mL) was added K2C03 (5.37 g, 38.9 mmol) followed by addition of 3-bromoprop-1-ene (3-g) (3.14 g, 25.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-g (1.8 g, crude). LCMS: 195.05 (M+1).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 72a.1 Step 1: Synthesis of l-(3-(allyloxy)-4-fluorophenyl)ethan-l-one (3-g) To a stirred solution of 1-g (2.0 g, 12.9 mmol) in DMF (10 mL) was added K2CO3 (5.37 g, 38.9 mmol) followed by addition of 3-bromoprop-l-ene (3-g) (3.14 g, 25.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtO Ac. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 3-g (1.8 g, crude). LCMS: 195.05 (M+l).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 72a.1 Step 1: Synthesis of 1-(3-(cyclopropylmethoxy)-2-fluorophenyl)ethan- 1-one (3-e) To a stirred solution of 1-e (3.0 g, 19.4 mmol) in DMF (30 mL) was added K2C03 (8.0 g,58.4 mmol) followed by addition of (bromomethyl)cyclopropane (2-e) (3.1 g, 23.3 mmol) and the reaction mixture was refluxed for 4 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-e (3.4 g, crude).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 72a.1 Production Example 72a: Synthesis of (S)-N-(1-(3-(allyloxy)-4-fluorophenyl) ethyl)-5- (2,4-dioxoimidazolidin-1-yl)pentane-1-sulfonamide Scheme 7. Step 1: Synthesis of 1-(3-(allyloxy)-4-fluorophenyl)ethan-1-one (3-g) To a stirred solution of 1-g (2.0 g, 12.9 mmol) in DMF (10 mL) was added K2CO3 (5.37 g, 38.9 mmol) followed by addition of 3-bromoprop-1-ene (3-g) (3.14 g, 25.9 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-g (1.8 g, crude). LCMS: 195.05 (M+1).

  • 33
  • [ 36982-56-6 ]
  • [ 949159-95-9 ]
  • 1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 73a.1 106331 Step 1: Synthesis of 1-(3-(2-cvclopropyethoxv)-4-t1uorophenvl)ethan-1-one (3-h) To a stirred solution of i-h (2.6 g, 16.8 mrnol) in DMF (25 mL) was added K2C03 (4.65 g, 33.7 mmol) followed by (2-bromoethyl)cyciopropane (3.0 g, 20.2 rnrnol) and the reaction mixture was refiuxed for 2 h (reaction deemed complete by TLC). The reaction mixture wasquenched with water and extracted with EtOAc, The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afthrd3-h (3.5g, crude). LCMS: 223i5 (M+i).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 73a.1 Step 1: Synthesis of l-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-l-one (3- h) To a stirred solution of 1-h (2.6 g, 16.8 mmol) in DMF (25 mL) was added K2CO3(4.65 g, 33.7 mmol) followed by (2-bromoethyl)cyclopropane (3.0 g, 20.2 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtO Ac. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-h (3.5 g, crude). LCMS: 223.15 (M+l).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 73a.1 Step 1: Synthesis of 1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-1-one (3-h) To a stirred solution of 1-h (2.6 g, 16.8 mmol) in DMF (25 mL) was added K2C03 (4.65 g, 33.7 mmol) followed by (2-bromoethyl)cyclopropane (3.0 g, 20.2 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-h (3.5 g, crude). LCMS: 223.15 (M+1).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 73a.1 Step 1: Synthesis of l-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-l-one (3- h) To a stirred solution of 1-h (2.6 g, 16.8 mmol) in DMF (25 mL) was added K2CO3 (4.65 g, 33.7 mmol) followed by (2-bromoethyl)cyclopropane (3.0 g, 20.2 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-h (3.5 g, crude). LCMS: 223.15 (M+l).
With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; 73a.1 Step 1: Synthesis of 1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-1-one (3-h) To a stirred solution of 1-h (2.6 g, 16.8 mmol) in DMF (25 mL) was added K2C03 (4.65 g, 33.7 mmol) followed by (2-bromoethyl)cyclopropane (3.0 g, 20.2 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-h (3.5 g, crude). LCMS: 223.15 (M+1).
With potassium carbonate In N,N-dimethyl-formamide Reflux; 73a.1 Production Example 73a: Synthesis of (S)-N-(1-(3-(2-cyclopropylethoxy)-4- fluorophenyl) ethyl)-5-(2, 4-dioxoimidazolidin-1-yl) pentane-1-sulfonamide Scheme 8. [0681] Step 1: Synthesis of 1-(3-(2-cyclopropylethoxy)-4-fluorophenyl)ethan-1-one (3- h) To a stirred solution of 1-h (2.6 g, 16.8 mmol) in DMF (25 mL) was added K2CO3 (4.65 g, 33.7 mmol) followed by (2-bromoethyl)cyclopropane (3.0 g, 20.2 mmol) and the reaction mixture was refluxed for 2 h (reaction deemed complete by TLC). The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3-h (3.5 g, crude). LCMS: 223.15 (M+1).

  • 34
  • 2-(2-fluoro-5-acetylphenoxy)pyridine [ No CAS ]
  • [ 949159-95-9 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 2-(2-fluoro-5-acetylphenoxy)pyridine With methyl trifluoromethanesulfonate In toluene at 100℃; for 2h; Inert atmosphere; Stage #2: With sodium ethanolate for 1h; Reflux; Inert atmosphere; 12.3 A solution of 231 mg (1.0 mmol) of 2- (2-fluoro-5-acetylphenoxy)Was dissolved in 30 mL of toluene,Under the protection of argon, 200 μL (1.75 mmol) of methyl trifluoromethanesulfonate was added,The mixture was stirred at 100 ° C for 2 hours.The reaction solution was cooled to room temperature and toluene was removed under reduced pressure,The resulting residue was added under fresh nitrogen to a freshly prepared sodium ethoxide solution18 mL (0.69 g (30.0 mmol) of metallic sodiumDissolved in 18 mL of absolute ethanol)Then heated to reflux,The reaction was stirred for 1 hour,The obtained reaction solution was distilled off the solvent, and then 30 mL of water was added,And extracted with ethyl acetate (20 ml x 3)The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure.The residue was separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 20: 1)Collecting the eluate containing the product,The solvent was distilled off to give 120.1 mg of 2-fluoro-5-acetylphenol (77% yield by gas chromatography).
  • 35
  • [ 949159-95-9 ]
  • 2-bromo-1-(4-fluoro-3-hydroxyphenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper(ll) bromide In chloroform; ethyl acetate for 8h; Reflux; 26 Preparation of 2-bromo-1-(4-fluoro-3-hydroxyphenyl)ethanone 4'-fluoro-3'-hydroxyacetophenone (100 mg, 0.649 mmol), copper (II) bromide, (174 mg, 0.779 mmol) In ethyl acetate (5 mL) / chloroform (5 mL) Was refluxed for 8 hours. The reaction mixture was filtered to remove copper (I) bromide. The filtrate was concentrated in vacuo to give 2-bromo-1- (4-fluoro-3-hydroxyphenyl) ethanone (123 mg, 81%) as a yellow solid.
81% With copper(ll) bromide In chloroform; ethyl acetate for 8h; Reflux;
  • 36
  • [ 24964-64-5 ]
  • [ 949159-95-9 ]
  • (E)-3-(3-(4-fluoro-3-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With boron trifluoride diethyl etherate In 1,4-dioxane at 80℃;
  • 37
  • [ 105-07-7 ]
  • [ 949159-95-9 ]
  • (E)-4-(3-(4-fluoro-3-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With boron trifluoride diethyl etherate In 1,4-dioxane at 80℃;
  • 38
  • [ 509072-57-5 ]
  • [ 949159-95-9 ]
  • C12H11F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%)
  • 39
  • 3-tetrahydrofuranmethanol [ No CAS ]
  • [ 949159-95-9 ]
  • C13H15FO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%)
  • 40
  • [ 97-99-4 ]
  • [ 949159-95-9 ]
  • C13H15FO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%)
  • 41
  • [ 96-41-3 ]
  • [ 949159-95-9 ]
  • C13H15FO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%)
  • 42
  • [ 459-56-3 ]
  • [ 949159-95-9 ]
  • C15H12F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%)
  • 43
  • [ 5720-05-8 ]
  • [ 949159-95-9 ]
  • 1-(4-fluoro-3-(p-tolyloxy)phenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With pyridine; copper diacetate In dichloromethane at 20℃; for 72h; Step 1: 1-(4-Fluoro-3-(p-tolyloxy)phenyl)ethan-1-one: A mixture containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.5 g, 3.24 mmol), p-tolylboronic acid (0.88 g, 6.48 mmol), Cu(OAc)2 (1.176g, 6.48 mmol), and pyridine (0.52 mL, 6.48 mmol) in dichloromethane (11 mL) was stirred for 72 hr atroom temperature. The reaction mixture was quenched by the addition of 1 N HCl (5 mL), extracted withdichloromethane (3 x 15 mL), and dried over MgSO4. The combined organic layers were concentratedunder reduced pressure and the residue was purified by column chromatography (0 to 20 %Hexanes/EtOAc gradient) to afford 1-(4-fluoro-3-(p-tolyloxy)phenyl)ethan-1-one as an oil (355 mg, 45%). LCMS RT: 1.10 min; MS (ES) m/z = 245.3 [M+H]+.
  • 44
  • [ 949159-95-9 ]
  • [ 108-95-2 ]
  • [ 147379-67-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper diacetate In dichloromethane at 20℃; for 72h; Step 1: 1-(4-Fluoro-3-(p-tolyloxy)phenyl)ethan-1-one: A mixture containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.5 g, 3.24 mmol), p-tolylboronic acid (0.88 g, 6.48 mmol), Cu(OAc)2 (1.176g, 6.48 mmol), and pyridine (0.52 mL, 6.48 mmol) in dichloromethane (11 mL) was stirred for 72 hr atroom temperature. The reaction mixture was quenched by the addition of 1 N HCl (5 mL), extracted withdichloromethane (3 x 15 mL), and dried over MgSO4. The combined organic layers were concentratedunder reduced pressure and the residue was purified by column chromatography (0 to 20 %Hexanes/EtOAc gradient) to afford 1-(4-fluoro-3-(p-tolyloxy)phenyl)ethan-1-one as an oil (355 mg, 45%). LCMS RT: 1.10 min; MS (ES) m/z = 245.3 [M+H]+.
  • 45
  • [ 372-20-3 ]
  • [ 949159-95-9 ]
  • C14H10F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper diacetate In dichloromethane at 20℃; for 72h; Step 1: 1-(4-Fluoro-3-(p-tolyloxy)phenyl)ethan-1-one: General procedure: A mixture containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.5 g, 3.24 mmol), p-tolylboronic acid (0.88 g, 6.48 mmol), Cu(OAc)2 (1.176g, 6.48 mmol), and pyridine (0.52 mL, 6.48 mmol) in dichloromethane (11 mL) was stirred for 72 hr atroom temperature. The reaction mixture was quenched by the addition of 1 N HCl (5 mL), extracted withdichloromethane (3 x 15 mL), and dried over MgSO4. The combined organic layers were concentratedunder reduced pressure and the residue was purified by column chromatography (0 to 20 %Hexanes/EtOAc gradient) to afford 1-(4-fluoro-3-(p-tolyloxy)phenyl)ethan-1-one as an oil (355 mg, 45%). LCMS RT: 1.10 min; MS (ES) m/z = 245.3 [M+H]+.
  • 46
  • [ 371-41-5 ]
  • [ 949159-95-9 ]
  • C14H10F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper diacetate In dichloromethane at 20℃; for 72h; Step 1: 1-(4-Fluoro-3-(p-tolyloxy)phenyl)ethan-1-one: General procedure: A mixture containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.5 g, 3.24 mmol), p-tolylboronic acid (0.88 g, 6.48 mmol), Cu(OAc)2 (1.176g, 6.48 mmol), and pyridine (0.52 mL, 6.48 mmol) in dichloromethane (11 mL) was stirred for 72 hr atroom temperature. The reaction mixture was quenched by the addition of 1 N HCl (5 mL), extracted withdichloromethane (3 x 15 mL), and dried over MgSO4. The combined organic layers were concentratedunder reduced pressure and the residue was purified by column chromatography (0 to 20 %Hexanes/EtOAc gradient) to afford 1-(4-fluoro-3-(p-tolyloxy)phenyl)ethan-1-one as an oil (355 mg, 45%). LCMS RT: 1.10 min; MS (ES) m/z = 245.3 [M+H]+.
  • 47
  • [ 402-45-9 ]
  • [ 949159-95-9 ]
  • C15H10F4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper diacetate In dichloromethane at 20℃; for 72h; Step 1: 1-(4-Fluoro-3-(p-tolyloxy)phenyl)ethan-1-one: General procedure: A mixture containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.5 g, 3.24 mmol), p-tolylboronic acid (0.88 g, 6.48 mmol), Cu(OAc)2 (1.176g, 6.48 mmol), and pyridine (0.52 mL, 6.48 mmol) in dichloromethane (11 mL) was stirred for 72 hr atroom temperature. The reaction mixture was quenched by the addition of 1 N HCl (5 mL), extracted withdichloromethane (3 x 15 mL), and dried over MgSO4. The combined organic layers were concentratedunder reduced pressure and the residue was purified by column chromatography (0 to 20 %Hexanes/EtOAc gradient) to afford 1-(4-fluoro-3-(p-tolyloxy)phenyl)ethan-1-one as an oil (355 mg, 45%). LCMS RT: 1.10 min; MS (ES) m/z = 245.3 [M+H]+.
  • 48
  • [ 456-47-3 ]
  • [ 949159-95-9 ]
  • C15H12F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%)
  • 49
  • [ 4333-56-6 ]
  • [ 949159-95-9 ]
  • 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Step 1: 1-(3-Cyclopropoxy-4-fluorophenyl)ethan-1-one. To a solution containing 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one (0.3 g, 1.94 mmol) and anhydrousDMF was added potassium carbonate (1.6 g, 11.6 mmol) and cyclopropyl bromide (0.62 mL, 7.76 mmol).The reaction mixture was heated at 160 oC for 60 min in a microwave reactor, then poured into waterand extracted with ethyl acetate (3 x 40 mL). The organic layers were washed with brine (2 x 50 mL) anddried with anhydrous magnesium sulfate. The solvents were removed under reduced pressure andpurified by purified by silica gel chromatography (Combi-flash Rf, hexane/ethyl acetate, 0-20% gradient)to give 1-(3-cyclopropoxy-4-fluorophenyl)ethan-1-one (173 mg, 46%) MS (ES) m/z = 195.1 [M+H]+; LCMSRT = 0.99 min. 1H NMR (CDCl3) δ 7.90 (dd, J = 12, 4 Hz, 1H), 7.55-7.52 (m, 1H), 7.11 (dd, J = 12, 4 Hz, 1H),3.89-3.86 (m, 1H), 2.59 (s, 3H), 0.86-0.83 (m, 4H).
  • 50
  • [ 120-14-9 ]
  • [ 949159-95-9 ]
  • (E)-3-(3,4-dimethoxyphenyl)-1-(4-fluoro-3-hydroxyphenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With potassium hydroxide In ethanol; water at 0 - 20℃; for 4h; 34 (E)-3-(3,4-dimethoxyphenyl)-1-(4-fluoro-3-hydroxyphenyl)prop-2-en-1-one (3). To the solution of 3,4-dimethoxybenzaldehyde 1 (6.391 g, 38.5 mmol) and 1-(4-fluoro-5-hydroxyphenyl)ethan-1-one 2 (5.39 g, 35 mmol) in EtOH (70 mL) was added a solution of 40% aqueous KOH (19.6 g, 140 mmol) at 0° C. The resulting solution was reacted at room temperature for 4 h. The yellow solid was filtrated to give compound 3 (9.368 g, 89%). [M+H]+=303.2
  • 51
  • 2-propylpentyl methanesulfonate [ No CAS ]
  • [ 949159-95-9 ]
  • 1-(4-fluoro-3-((2-propylpentyl)oxy)phenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 1-(4-fluoro-3-hydroxyphenyl)ethan-1-one With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: 2-propylpentyl methanesulfonate In N,N-dimethyl-formamide at 85℃; Inert atmosphere;
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