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[ CAS No. 157652-28-3 ] {[proInfo.proName]}

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Chemical Structure| 157652-28-3
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Product Details of [ 157652-28-3 ]

CAS No. :157652-28-3 MDL No. :MFCD11505951
Formula : C9H8BrFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DAYFMDZWYCRYEJ-UHFFFAOYSA-N
M.W : 247.06 Pubchem ID :18323864
Synonyms :

Safety of [ 157652-28-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 157652-28-3 ]

* 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 [ 157652-28-3 ]

[ 157652-28-3 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 157652-28-3 ]
  • [ 17356-08-0 ]
  • [ 199873-35-3 ]
YieldReaction ConditionsOperation in experiment
79% In methanol for 48h; Heating / reflux; 147 Example 147
Preparation of 2-carbomethoxy-5-fluorobenzyl thiouronium hydrochloride The compound of Example 146 (7.016 g, 25.6 mmole based on 90% purity) and thiourea (1.9 g, 26 mmol) were refluxed in methanol (50 mL) for 48 h. The residue was dissolved in water (300 mL), and washed with diethyl ether (3×400 mL). The solvent was removed from the aqueous layer. The resultant yellow solid was dissolved in water (500 mL), Bio-Rex 5 resin (25 g of prewashed resin, chloride form, 8.8 meq/dry g) was added, and the heterogenous solution was stirred for 1 h. The solution was filtered. The treatment with resin was repeated, and the solution was filtered. The solvent was removed. The residue was dissolved in methanol, and the solvent was removed in vacuo to afford 5.65 g of a light yellow solid (79% yield).
  • 2
  • [ 174403-69-1 ]
  • [ 157652-28-3 ]
YieldReaction ConditionsOperation in experiment
94% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; Example 146 Preparation of 2-carbomethoxy-5-fluorobenzyl bromide STR222 A suspension of the compound of Example 145 (5.1 g, 30 mmol), N-bromosuccinimide (5.4 g, 30 mmol) and benzoyl peroxide (0.073 g, 0.30 mmol) in carbon tetrachloride (115 mL) was refluxed for 18 h. The reaction mixture was cooled to 0 C., filtered, and the precipitate was washed with diethyl ether. The solvent was removed in vacuo to afford 7.02 g (94% crude yield) of the title compound, contaminated with a small amount of succinimide. Rf =0.48 20% ethyl acetate/hexanes.
94% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 18h;Heating / reflux; A suspension of the compound of Example 145 (5.1 g, 30 mmol), N-bromosuccinimide (5.4 g, 30 mmol) and benzoyl peroxide (0.073 g, 0.30 mmol) in carbon tetrachloride (115 mL) was refluxed for 18 h. The reaction mixture was cooled to 0 C., filtered, and the precipitate was washed with diethyl ether. The solvent was removed in vacuo to afford 7.02 g (94% crude yield) of the title compound, contaminated with a small amount of succinimide. Rf=0.48 20% ethyl acetate/hexanes.
87% With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; at 80℃; for 8h; Step 2: To a solution of compound 32 (6.3 g, 41.4 mmol) in DCE (100 mL) was added NBS (8.1 g, 46 mmol) followed by a catalytic amount of benzoyl peroxide (200 mg, 0.82 mmol). The reaction was then heated at 80 C for 8 hrs. The reaction was cooled to room temperature and the precipitated solid was removed by filtration and washed with MTBE. The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaOH (150 mL) and MTBE (150 mL). The organic layer was separated, dried over MgS04, filtered and concentrated to give compound 33 (8.9 g, 87% yield). 1H NMR (400 MHz, CDCI3) delta 8.05 (1 H, m), 7.20 (1 H, m), 7.10 (1 H, m), 4.90 (2 H, s), 3.95 (3 H, s).
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3h;Inert atmosphere; Reflux; A mixture of <strong>[174403-69-1]4-fluoro-2-methyl-benzoic acid methyl ester</strong> (12.7 g, 75.5 mmol), NBS (13.4 g, 75.5 mmol), and di-benzoyl peroxide (BPO) (0.85 g, 3.5 mmol) in CC (200 mL) was heated to reflux for 3 hours until all starting material was consumed. After vacuum filration, the filtrate concentrated in vacuo to give a crude product (17 g, yield 91%), which was used in the next step reaction without further purification.

  • 3
  • [ 157652-28-3 ]
  • [ 199873-35-3 ]
YieldReaction ConditionsOperation in experiment
79% With thiourea In methanol; water 147 Preparation of 2-carbomethoxy-5-fluorobenzyl thiouronium hydrochloride STR223 Example 147 Preparation of 2-carbomethoxy-5-fluorobenzyl thiouronium hydrochloride STR223 The compound of Example 146 (7.016 g, 25.6 mmole based on 90% purity) and thiourea (1.9 g, 26 mmol) were refluxed in methanol (50 mL) for 48 h. The residue was dissolved in water (300 mL), and washed with diethyl ether (3*400 mL). The solvent was removed from the aqueous layer. The resultant yellow solid was dissolved in water (500 mL), Bio-Rex 5 resin (25 g of prewashed resin, chloride form, 8.8 meq/dry g) was added, and the heterogenous solution was stirred for 1 h. The solution was filtered. The treatment with resin was repeated, and the solution was filtered. The solvent was removed. The residue was dissolved in methanol, and the solvent was removed in vacuo to afford 5.65 g of a light yellow solid (79% yield).
  • 4
  • [ 157652-28-3 ]
  • [ 99-98-9 ]
  • [ 1022984-21-9 ]
YieldReaction ConditionsOperation in experiment
With acetic acid Heating;
  • 5
  • [ 321-21-1 ]
  • [ 157652-28-3 ]
  • 6
  • [ 157652-28-3 ]
  • [ 2393-23-9 ]
  • [ 1440519-88-9 ]
YieldReaction ConditionsOperation in experiment
13 g In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere; C [C] 5-Fluoro-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol- 1 -one To a stirred solution of 2-bromomethyl-4-fluoro-benzoic acid methyl ester (17 g, 68.8 mmol) in THF (200 mL) was added PMBNH2 (23.6 g, 172 mmol) at 0 °C. After stirring at room temperature for 16 hours, the reaction mixture was concentrated in vacuo to give a crude product which was then purified by column chromaography to give the title compound (13 g, yield 69%) as a solid.
  • 8
  • [ 157652-28-3 ]
  • C27H30FN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 5 h / 50 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 75 °C 2.2: 2 h / 80 °C
  • 9
  • [ 157652-28-3 ]
  • C26H28FN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 5 h / 50 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 75 °C 2.2: 2 h / 80 °C 3.1: lithium hydroxide / methanol / 20 °C
  • 10
  • [ 157652-28-3 ]
  • [ 39903-01-0 ]
  • methyl 2-(((2-amino-5-bromopyridin-3-yl)oxy)methyl)-4-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With caesium carbonate; In acetonitrile; at 50℃; for 5h; Step 3: To compound 33 (15.0 g, 61 mmol) in acetonitrile (150 mL) at room temperature was added compound 34 (10.9 g, 58 mmol) followed by cesium carbonate (23 g, 69 mmol). The mixture was then heated at 50 °C for 5 hours before cooling to room temperature. The mixture was then concentrated in vacuo to remove ~ 80percent of the acetonitrile before the residue was partitioned between water (400 mL) and ethyl acetate (400 mL). The two layers were separated and the aqueous layer was re-extracted with ethyl acetate (400 mL). The combined organics were then concentrated in vacuo to give a dark brown solid. (Note that the aqueous layer was still very dark and contained insoluble solids - yield likely to be compromised by the lack of solubility of the product in organic solvents). The solid residue was then slurried in MTBE (300 mL) for 20 minutes and compound 35 was collected as a dark grey solid (1 1 .5 g, 52percent yield. This product was then purified further by column chromatography on silica gel eluting with ethyl acetate and cyclohexane (33percent EtOAc to neat EtOAc) to give compound 35 (9.5 g, 44percent yield) as an off- white solid. 1H NMR (400 MHz, CDCI3) delta 8.10 (1 H, m), 7.75 (1 H, s), 7.35 (1 H, m), 7.10 (1 H, m), 7.05 (1 H, s), 5.50 (2 H, s), 4.75 (1 H, br s), 3.90 (3 H, s). LCMS ES m/z 355/357 [M+H]+.
  • 11
  • [ 157652-28-3 ]
  • 7-amino-12-fluoro-1,3,16-trimethyl-16,17-dihydro-1H-8,4-(metheno)pyrazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecin-15(10H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / acetonitrile / 5 h / 50 °C 2: palladium diacetate; bis(pinacol)diborane; cataCXium A; cesium fluoride / methanol; water / 3 h / 60 °C 3: sodium hydroxide / methanol; water / 3.5 h / 40 °C 4: hydrogenchloride / methanol; 1,4-dioxane / 2.5 h / 40 °C 5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 0 °C
  • 14
  • [ 157652-28-3 ]
  • C20H22FN5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / acetonitrile / 5 h / 50 °C 2: palladium diacetate; bis(pinacol)diborane; cataCXium A; cesium fluoride / methanol; water / 3 h / 60 °C 3: sodium hydroxide / methanol; water / 3.5 h / 40 °C 4: hydrogenchloride / methanol; 1,4-dioxane / 2.5 h / 40 °C
  • 15
  • [ 157652-28-3 ]
  • 2-([2-amino-5-(3-[(tert-butoxycarbonyl)(methyl)amino]methyl}-5-cyano-1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]oxy}methyl)-4-fluorobenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 5 h / 50 °C / Inert atmosphere 2.1: palladium diacetate; cesium fluoride; catacxium A; bis(pinacol)diborane / methanol; toluene; water / 0.5 h / 60 - 100 °C / Inert atmosphere 2.2: 5 h / 100 °C / Inert atmosphere 3.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere
  • 16
  • [ 157652-28-3 ]
  • 7-amino-12-fluoro-2,16-dimethyl-15-oxo-10,15,16,17-tetrahydro-2H-8,4-(metheno)pyrazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / acetonitrile / 5 h / 50 °C / Inert atmosphere 2.1: palladium diacetate; cesium fluoride; catacxium A; bis(pinacol)diborane / methanol; toluene; water / 0.5 h / 60 - 100 °C / Inert atmosphere 2.2: 5 h / 100 °C / Inert atmosphere 3.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 4.1: dichloromethane / 20 h / 20 °C / Inert atmosphere 5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.42 h / 20 °C / Inert atmosphere
  • 17
  • [ 157652-28-3 ]
  • methyl 2-([2-amino-5-(3-[(tert-butoxycarbonyl)(methyl)amino]methyl}-5-cyano-1-methyl-1Hpyrazol-4-yl)pyridin-3-yl]oxy}methyl)-4-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 5 h / 50 °C / Inert atmosphere 2.1: palladium diacetate; cesium fluoride; catacxium A; bis(pinacol)diborane / methanol; toluene; water / 0.5 h / 60 - 100 °C / Inert atmosphere 2.2: 5 h / 100 °C / Inert atmosphere
  • 18
  • [ 157652-28-3 ]
  • 2-[(2-amino-5-{5-cyano-1-methyl-3-[(methylamino)methyl]-1H-pyrazol-4-yl}pyridin-3-yl)oxy]methyl}-4-fluorobenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / acetonitrile / 5 h / 50 °C / Inert atmosphere 2.1: palladium diacetate; cesium fluoride; catacxium A; bis(pinacol)diborane / methanol; toluene; water / 0.5 h / 60 - 100 °C / Inert atmosphere 2.2: 5 h / 100 °C / Inert atmosphere 3.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 4.1: dichloromethane / 20 h / 20 °C / Inert atmosphere
  • 19
  • [ 157652-28-3 ]
  • (S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-amine [ No CAS ]
  • 2-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)-4-fluoroisoindolin-1-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.23 g With triethylamine In toluene for 2h; Reflux; 58 EXAMPLE 58: 2-((S)- 1-(((S)-2,3-Dihydrobenzo [bj [1 ,4]dioxin-2-yl)methyl)piperidin-3- yl)-5-fluoroisoindolin-1-one hydrochloride A mixture of (5)-i -(((S)-2,3-dihydrobenzo[b] [1 ,4]dioxin-2-yl)methyl)piperidin-3-amine (0.25 g, 1.01 mmol), methyl 2-(bromomethyl)-4-fluorobenzoate (0.25 g, 1.01 mmol) and TEA (0.21 ml, 0.15 g, 1.51 mmol) in toluene (7 ml) was refluxed for 2 h. The precipitate was filtered off and the filtrate evaporated to dryness. The residue was purified by flash chromatography yielding 0.23 g 2-((S)- 1 -(((5)-2,3 -dihydrobenzo[b] [1,4] dioxin-2-yl)methyl)piperidin-3 -yl)-4-fluoroisoindolin- i-one hydrochloride after conversion of free base to HC1 salt in EtOAc.‘H NMR (400 MHz, DMSO-d6) ö ppm 1.77-2.11 (4H, m), 2.99-3.18 (1H, m), 3.32-3.68 (5H, m), 4.00-4.10 (1H, m), 4.31-4.40 (1H, m), 4.48-4.69 (3H, m), 4.86-5.00 (1H, m), 6.83- 6.97 (4H, m), 7.31-7.39 (1H, m), 7.51-7.58 (1H, m), 7.73-7.81 (1H, m), 11.05 (1H, brs).
  • 20
  • [ 157652-28-3 ]
  • C25H22FN3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone 2.1: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice 3.1: polyphosphoric acid / 1 h / 60 - 140 °C 4.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice 5.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 3 h / 100 °C / Sealed tube 6.1: lithium chloride / N,N-dimethyl acetamide / 3 h / 100 °C 6.2: 0.25 h / 20 °C
  • 21
  • [ 157652-28-3 ]
  • 4-fluoro-2-[(phenylthio)methyl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice
  • 22
  • [ 157652-28-3 ]
  • 8-fluorodibenzo[b,e]thiepin-11(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetone 2: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice 3: polyphosphoric acid / 1 h / 60 - 140 °C
  • 23
  • [ 157652-28-3 ]
  • 8-fluoro-6,11-dihydrodibenzo[b,e]thiepin-11-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / acetone 2: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice 3: polyphosphoric acid / 1 h / 60 - 140 °C 4: methanol; sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice
  • 24
  • [ 157652-28-3 ]
  • C32H28FN3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone 2: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice 3: polyphosphoric acid / 1 h / 60 - 140 °C 4: methanol; sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice 5: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 4 h / 100 °C / Sealed tube
  • 25
  • [ 157652-28-3 ]
  • C25H22FN3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone 2.1: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice 3.1: polyphosphoric acid / 1 h / 60 - 140 °C 4.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice 5.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 4 h / 100 °C / Sealed tube 6.1: lithium chloride / N,N-dimethyl acetamide / 4 h / 100 °C 6.2: 20 °C
  • 26
  • [ 157652-28-3 ]
  • C32H28FN3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone 2: sodium hydroxide / tetrahydrofuran; methanol / Cooling with ice 3: polyphosphoric acid / 1 h / 60 - 140 °C 4: methanol; sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice 5: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 3 h / 100 °C / Sealed tube
  • 27
  • [ 157652-28-3 ]
  • [ 108-98-5 ]
  • C15H13FO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone 5.1 first step To a suspension of compound 51 (19.2 g, 77.8 mmol) and potassium carbonate (16.13 g, 117 mmol) in acetone (190 mL) was added thiophenol (8.01 mL, 78 mmol) And stirred for a while. The reaction solution was cooled to 25 ° C., ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed twice with water and concentrated under reduced pressure to obtain compound 52.
  • 28
  • [ 157652-28-3 ]
  • 4-fluoro-2-[(phenoxy)methyl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide / ethanol; water / 1 h / 100 °C
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide; water / ethanol
  • 29
  • [ 157652-28-3 ]
  • C14H10ClFO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide / ethanol; water / 1 h / 100 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
  • 30
  • [ 157652-28-3 ]
  • 8-fluorodibenzo[b,e]oxepin-11(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide / ethanol; water / 1 h / 100 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 4.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide; water / ethanol 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 3.2: 0 - 20 °C
  • 31
  • [ 157652-28-3 ]
  • (Z)-3-(8-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine [ No CAS ]
  • (E)-3-(8-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide / ethanol; water / 1 h / 100 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 4.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C 5.1: iodine; magnesium / tetrahydrofuran / Reflux 5.2: 2 h / 65 °C / Inert atmosphere 5.3: 1 h / Inert atmosphere
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 80 °C 2.1: sodium hydroxide; water / ethanol 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 3.2: 0 - 20 °C 4.1: magnesium; iodine / tetrahydrofuran / Heating 4.2: 2 h / 65 °C / Inert atmosphere
  • 32
  • [ 157652-28-3 ]
  • [ 108-95-2 ]
  • methyl 4-fluoro-2-(phenoxymethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2-bromomethyl-4-fluoro-benzoic acid methyl ester In N,N-dimethyl-formamide at 80℃; for 3h;
61% Stage #1: phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2-bromomethyl-4-fluoro-benzoic acid methyl ester In N,N-dimethyl-formamide at 80℃; for 3h; 1 The solution of phenol (119 mg, 1.26 mmol) in DMF was added K2CO3,the mixture was stirred at room temperature for 10 min, then methyl 2- (bromomethyl) -4-fluorobenzoate (260 mg, 1.0 mmol) was added to the above mixture and stirred at 80 for 3 hours. After completion of the reaction, the mixture was poured into water and extracted with EtOAc. The organic layer was concentrated and purified by column chromatography (silica gel, petroleum ether/Ethyl acetate = 40 : 1) to give methyl 4-fluoro-2- (phenoxymethyl) benzoate (160 mg, yield 61%) .1H NMR (400 MHz, Chloroform-d ) : δ (ppm) 8.10 (dd, J = 8.6, 5.8 HZ, 1H) , 7.50 (dd, J = 10.1, 2.5 Hz 1H) , 7.26 -7.31 (m, 2H) , 6.99 -7.02 (m,4H) , 5.50 (s, 2H) , 3.91 (s, 3H) .
  • 33
  • [ 157652-28-3 ]
  • (5′S)-10′-fluoro-6′-methyl-5′,6′-dihydro-3′H-spiro[cyclopropane-1,4′-[2,6]diaza[2,5]methano[2,6]benzodiazonin]-7′(1′H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / dichloromethane / 14 h 2: lithium hydroxide / methanol; tetrahydrofuran; water / 12 h 3: hydrogenchloride / water; 1,4-dioxane; ethyl acetate / 5 h / 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h
  • 34
  • [ 157652-28-3 ]
  • C20H27FN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 14 h 2: lithium hydroxide / methanol; tetrahydrofuran; water / 12 h
  • 35
  • [ 157652-28-3 ]
  • ClH*C15H19FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / dichloromethane / 14 h 2: lithium hydroxide / methanol; tetrahydrofuran; water / 12 h 3: hydrogenchloride / water; 1,4-dioxane; ethyl acetate / 5 h / 20 °C
  • 36
  • [ 157652-28-3 ]
  • tert-butyl N-[(7S)-5-azaspiro[2.4]heptan-7-yl]-N-methylcarbamate [ No CAS ]
  • methyl 2-({(7S)-7-[(tert-butoxycarbonyl)(methyl)amino]-5-azaspiro[2.4]heptan-5-yl}methyl)-4-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In dichloromethane for 14h; 5.1.18 Methyl 2-({(7S)-7-[(tert-butoxycarbonyl)(methyl)amino]-5-azaspiro[2.4]heptan-5-yl}methyl)-4-fluorobenzoate (21b) To a solution of tert-butyl (7S)-5-azaspiro[2.4]heptan-7-yl(methyl)carbamate 9b (1.01g, 4.06mmol) in dichloromethane (40mL), methyl 2-(bromomethyl)-4-fluoro-benzoate (1.00g, 4.00mmol) and potassium carbonate (0.73g, 5.30mmol) were added and the resulting mixture was stirred for 14h. The mixture was poured into water, and the dichloromethane was separated. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel by eluting with 0%-20% methanol in dichloromethane to obtain the title compound 21b (1.24g, 78%) as an oil. 1H NMR (400MHz, CDCl3) δ: 7.86-7.82 (1H, m), 7.30 (1H, d, J=9.8Hz), 6.98 (1H, t, J=9.8Hz), 4.59-4.45 (1H, m), 3.96-3.90 (2H, m), 3.88 (3H, s), 2.91 (3H, s), 2.87-2.78 (2H, m), 2.69-2.65 (1H, m), 2.43 (1H, d, J=9.0Hz), 1.41 (9H, s), 0.83-0.44 (4H, m) ; HRMS (Positive ESI) m/z 393.2184 (393.2189 calcd for C21H29FN2O4+H).
  • 37
  • [ 157652-28-3 ]
  • (R)-7-bromo-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-1(2H)-one [ No CAS ]
  • (R)-2-((7-bromo-3-(methoxymethyl)-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-yl)methyl)-4-fluorobenzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
18.9g With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 34.6; 45.1 Step 1: Preparation of compound 34j The raw material (R)-7-bromo-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-1(2H)-one (34h, 12.0g) was dissolved in DMF (23mL), added cesium carbonate (37.7g) and 2-(bromomethyl)-4-fluorobenzoic acid methyl ester (34i, 37.7g), the reaction was reacted at room temperature for 16 hours, and LC-MS monitored the reaction to be completed. Quench with water (200mL), ethyl acetate (2 200mL) diluted the solution. The organic phases were separated and combined and washed with 5% aqueous lithium chloride solution (3 200mL). The organic phases were separated and dried with anhydrous sodium sulfate, filtered, and concentrated 20.0g of crude product. The crude product was slurried with petroleum ether and methyl tert-butyl ether (4:1) in volume ratio to obtain 14.7g of pure solid. The mother liquor was concentrated through the column (petroleum ether: ethyl acetate=3:1) to obtain 4.2g of pure product. The product was 18.9 g, namely compound 34j. LC-MS [M+H]+= 425.0.
  • 38
  • [ 157652-28-3 ]
  • [ 4318-56-3 ]
  • C14H12ClFN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.5% With tri-n-propylamine In N,N-dimethyl-formamide at 105℃; for 2.5h; 1-4 Example 2 Preparation of compound of formula I Methyl 2-bromomethyl-4-fluorobenzoate (60.8g, 0.246mol), 6-chloro-3-methyluracil (39.1g, 0.243mol) and tri-n-propylamine (73.22g, 0.51mol) Dissolved in DMF (900mL), Heat to 105°C and stir for 2.5 hours, then cool to room temperature, add ice water to the reaction liquid, filter, add dichloromethane and water to the filter cake for liquid separation, and dry the organic phase with MgSO4. After filtration and concentration, 52.8 g of solid compound of formula I was obtained by column chromatography, with a yield of 66.5% and an HPLC purity of 96.53%.
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