204205-33-4

Basic information

• Product Name: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone
• Synonyms: Prasugrel Intermediate 4;2-Bromo-2-(2-fluorophenyl);Ethanone, 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)-;2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone;Cylopropylcarbonyl-2-flurobenzyl bromide;2-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone;Chemical intermediate for Prasugrel;2-broMo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-one
• CAS NO: 204205-33-4
• Molecular Formula: C₁₁H₁₀BrFO
• Molecular Weight: 257.1
• EINECS: 1806241-263-5
• Mol File: 204205-33-4.mol

Chemical Properties

• Boiling Point: 293.012 °C at 760 mmHg
• Flash Point: 131.009 °C
• Appearance: /
• Density: 1.574 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone(204205-33-4)
• EPA Substance Registry System: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone(204205-33-4)

Safety Data

• Hazardous Substances Data: 204205-33-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone is used as a reagent for the synthesis of potent anti-oxidant agents. Its unique structure allows it to participate in chemical reactions that can lead to the development of new compounds with strong anti-oxidant properties, which are essential in the pharmaceutical industry for the treatment and prevention of various diseases and conditions associated with oxidative stress.
Used in Chemical Research:
In addition to its applications in the pharmaceutical industry, 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone is also used as a research tool in chemical laboratories. Its ability to participate in various chemical reactions makes it a valuable compound for studying reaction mechanisms, exploring new synthetic routes, and discovering novel compounds with potential applications in various fields.
Overall, 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone is a versatile reagent with significant applications in both the pharmaceutical industry and chemical research, primarily due to its unique molecular structure and its role in the synthesis of potent anti-oxidant agents.

InChI:InChI=1/C11H10BrFO/c12-10(11(14)7-5-6-7)8-3-1-2-4-9(8)13/h1-4,7,10H,5-6H2

Synthetic route

1-cyclopropyl-2-(2-fluorophenyl)ethanone (150322-73-9) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
With iodine(I) bromide; 1-n-butyl-3-methylimidazolim bromide In tetrahydrofuran at 40℃; for 4h; Temperature; Time; Concentration;	95.3%
With bromine In methanol at 25 - 30℃; for 6h; Concentration;	94.65%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile) In cyclohexane at 10℃; Product distribution / selectivity; Reflux;	93.28%

(2-fluorophenyl)acetic acid (451-82-1) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.25 h / 0 - 5 °C 1.2: 6 h / 0 - 5 °C 2.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C 2.2: 40 - 50 °C 2.3: 0.25 h / 0 - 30 °C 3.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 1.2: 5 - 65 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 1.2: 5 - 65 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / toluene; dimethyl sulfoxide / 1.5 h / 95 - 110 °C / Large scale 2: bromine / methanol / Large scale View Scheme

2-(2-fluorophenyl)-N-methoxy-N-methylacetamide (946402-23-9) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C 1.2: 40 - 50 °C 1.3: 0.25 h / 0 - 30 °C 2.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 40 - 50 °C 1.2: 0.25 h / 0 - 30 °C 2.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / toluene-4-sulfonic acid / dichloromethane / 4.75 h / 0 - 5 °C / Reflux View Scheme

2-fluorobenzyl chloride (345-35-7) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide / dichloromethane; water / 25 °C 2.1: sodium hydroxide; water / 5 - 95 °C 2.2: pH 2 - 3 3.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 3.2: 5 - 65 °C 4.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide / dichloromethane; water / 25 °C 2.1: sodium hydroxide; water / 5 - 95 °C 2.2: pH 2 - 3 3.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 3.2: 5 - 65 °C 4.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: magnesium; iodine / tetrahydrofuran; 2-methyltetrahydrofuran / 1.5 h / 40 - 45 °C / Inert atmosphere 2: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: magnesium; iodine / tetrahydrofuran; toluene / 1.5 h / 40 - 45 °C / Inert atmosphere 2: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C View Scheme

2-fluorophenyl acetonitrile (326-62-5) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 5 - 95 °C 1.2: pH 2 - 3 2.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 2.2: 5 - 65 °C 3.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 5 - 95 °C 1.2: pH 2 - 3 2.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 2.2: 5 - 65 °C 3.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme

ethyl cyclopropylcarboxylate (4606-07-9) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Stage #1: With iodine; magnesium; isopropyl bromide In tetrahydrofuran at 65℃; for 3h; Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran at 5 - 70℃; for 3.16667h; Stage #3: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid In chloroform at 28 - 65℃; for 4h;

2-(2-fluorophenyl acetic acid) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 6 h / 0 - 5 °C 2.1: iodine; magnesium / tetrahydrofuran / 40 - 50 °C 2.2: 0.25 h / 0 - 30 °C 3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / toluene-4-sulfonic acid / dichloromethane / 4.75 h / 0 - 5 °C / Reflux View Scheme

fluorobenzene (462-06-6) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: tin(IV) chloride / tetrahydrofuran / 4 h / 45 °C 2: dichloromethane / 4 h / 20 °C 3: bromine / tetrahydrofuran / 10 h / 20 °C View Scheme

methyl o-fluorophenylacetate (57486-67-6) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 6 h / 20 - 60 °C 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 8 h / 20 °C View Scheme

o-fluorobenzyl bromide (446-48-0) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / methyl iodide / diethyl ether / 20 °C 1.2: 20 °C 1.3: 0 °C 2.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile) / cyclohexane / 10 °C / Reflux View Scheme

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (150322-38-6)

Conditions	Yield
With ammonium bicarbonate In dichloromethane at 5 - 20℃;	98%
With copper(l) iodide; sodium carbonate; XPhos In 1,4-dioxane at 60℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;	90.2%
With potassium phosphate; iodine In 1,4-dioxane at 80℃; for 4h; Temperature; Time; Reagent/catalyst;	87.6%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + N-allyl isothiocyanate (57-06-7) + 4-aminoethylbenzene (589-16-2) → 3-allyl-2-(4'-ethylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 18h; regioselective reaction;	96%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	96%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-[1-(2-naphthenyl)ethyledene]hydrazinecarbothioamide (133477-39-1) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((1-(naphthalen-2-yl)ethylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.333333h; Hantzsch Thiazole Synthesis; Reflux;	96%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + p-toluidine (106-49-0) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-methylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 20h; Reagent/catalyst; Temperature; Time; regioselective reaction;	95%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-Ethoxyaniline (156-43-4) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-ethoxylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 14h; regioselective reaction;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 6-methoxy-tetral-4-one thiosemicarbazone (304458-95-5) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.5h; Reagent/catalyst; Solvent; Temperature; Hantzsch Thiazole Synthesis; Reflux;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-Ethoxyaniline (156-43-4) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-ethoxylphenylimino)-4-cyclopropyl-5-(2'-fluoro-phenyl)-thiazole

Conditions	Yield
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 0.75h; regioselective reaction;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazinecarbothioamide (3689-17-6) → 4-cyclopropyl-2-((3,4-dihydronaphthalen-1(2H)-ylidene)hydrazono)-5-(2-fluorophenyl)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.5h; Hantzsch Thiazole Synthesis; Reflux;	94%

4-HYDROXYPIPERIDINE (5382-16-1) + 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) → 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4-hydroxypiperidine

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; water	93%
With potassium carbonate In N-methyl-acetamide; water	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) → (5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)boronic acid (1263407-24-4)

Conditions	Yield
Stage #1: C7H10BNO2S*C7H8O3S With triethylamine In ethanol at 50℃; Inert atmosphere; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In ethanol at 50℃; for 8h;	93%

+ 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) → 3-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)thiazolidine-2,4-dione (1563931-94-1)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 6h;	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-methoxy-aniline (104-94-9) + methyl thioisocyanate (556-61-6) → 3-methyl-2-(4'-methoxyphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 16h; regioselective reaction;	93%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.5h; regioselective reaction;	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 1-indanone thiosemicarbazone (74227-66-0) → 4-cyclopropyl-2-((2,3-dihydro-1H-inden-1-ylidene)hydrazono)-5-(2-fluorophenyl)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.333333h; Hantzsch Thiazole Synthesis; Reflux;	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + Ethyl isothiocyanate (542-85-8) + 4-aminoethylbenzene (589-16-2) → 3-ethyl-2-(4'-ethylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 14h; regioselective reaction;	92%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.5h; regioselective reaction;	92%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + Ethyl isothiocyanate (542-85-8) + 4-Ethoxyaniline (156-43-4) → 3-ethyl-2-(4'-ethoxyphenylimino)-4-cyclopropyl-5-(2'-fluoro-phenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 12h; regioselective reaction;	91%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 2h; regioselective reaction;	91%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 1-(1-(4-methoxyphenyl)ethylidene)thiosemicarbazide (16546-08-0) → 4-cyclopropyl-5-(2-fluorophenyl)-2-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)thiazole

Conditions	Yield
With triethylamine In ethanol for 0.583333h; Hantzsch Thiazole Synthesis; Reflux;	91%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride (109904-37-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (952340-38-4)

Conditions	Yield
Stage #1: 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride With triethylamine In dichloromethane at 10℃; for 0.25h; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 10℃; Stage #3: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone With triethylamine; sodium iodide In dichloromethane at 10 - 25℃; Temperature;	90%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 1-(1-(3,4-dimethoxyphenyl)ethylidene)thiosemicarbazide (71173-46-1) → 4-cyclopropyl-2-((1-(3,4-dimethoxyphenyl)ethylidene)hydrazono)-5-(2-fluorophenyl)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.666667h; Hantzsch Thiazole Synthesis; Reflux;	90%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-methoxy-aniline (104-94-9) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-methoxyphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 16h; regioselective reaction;	89%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 0.75h; regioselective reaction;	89%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-(1-(4-tolyl)ethylidene)hydrazinecarbothioamide (7410-54-0) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((1-(p-tolyl)ethylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.583333h; Hantzsch Thiazole Synthesis; Reflux;	89%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-bromo-aniline (106-40-1) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-bromophenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 20h; regioselective reaction;	88%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.25h; regioselective reaction;	88%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-[1-(4-nitrophenyl)ethylidene]hydrazine-1-carbothioamide (5424-45-3) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((1-(4-nitrophenyl)ethylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.5h; Hantzsch Thiazole Synthesis; Reflux;	88%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + C8H14BrNO2S → C19H23BrFNO3S

Conditions	Yield
With potassium phosphate; iodine at 80℃; for 7h; Temperature; Reagent/catalyst;	87.1%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + m-Anisidine (536-90-3) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(3'-methoxyphenylimino)-4-cyclopropyl-5-(2'-fluoro-phenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 18h; regioselective reaction;	87%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	87%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-chloro-aniline (106-47-8) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-chlorophenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 20h; regioselective reaction;	87%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.25h; regioselective reaction;	87%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-amino-phenol (123-30-8) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-hydroxyphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 24h; regioselective reaction;	82%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	82%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + (E)-4-(acetylsulfanyl)-3-((1-[(2-pyridyl)methyl]-1H-pyrazol-3-yl)methylidene)piperidine bis(hydrogen trifluoroacetate) → (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-((1-[(2-pyridyl)methyl]-1H-pyrazol-3-yl)methylidene)piperidine

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 0.5h;	81%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + (E)-4-(acetylsulfanyl)-3-((1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl)methylidene)piperidine hydrogen trifluoroacetate (853805-52-4) → (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-((1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl)methylidene)piperidine

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2.5h;	77%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + (E)-3-[(furan-2-yl)methylidene]piperidin-4-ol hydrogen acetate → (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-[(furan-2-yl)methylidene]piperidin-4-ol

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	74%

Upstream product

• 150322-73-9 1-cyclopropyl-2-(2-fluorophenyl)ethanone 
• 451-82-1 (2-fluorophenyl)acetic acid 
• 946402-23-9 2-(2-fluorophenyl)-N-methoxy-N-methylacetamide 
• 345-35-7 2-fluorobenzyl chloride 
• 326-62-5 2-fluorophenyl acetonitrile 
• 57486-67-6 methyl o-fluorophenylacetate 
• 446-48-0 o-fluorobenzyl bromide 
• 462-06-6 fluorobenzene 
• 4606-07-9 ethyl cyclopropylcarboxylate 

Downstream Products

• 150322-43-3 prasugel 
• 150322-38-6 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one 
• 1243654-57-0 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide 
• 150322-39-7 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride 
• 1287752-37-7 1-cyclopropyl-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-fluorophenyl)ethanone hydrobromide salt 
• 952340-38-4 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1190589-94-6 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide 
• 1060616-82-1 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydroiodide 
• 1306607-31-7 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate cyclamate 
• 1060616-79-6 prasugrel hydrobromide 
• 952340-40-8 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate benzene sulfonate 
• 951380-42-0 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 

Relevant articles and documents

2 - Bromo 2 - (2 - fluorophenyl) ethanone preparation of cyclopropyl (by machine translation)

The invention belongs to the technical field of medicines and particularly relates to a preparation method of a medicine intermediate, and more particularly relates to a preparation method of a prasugrel intermediate cyclopropyl-2-bromo-2-(2-fluorophenyl) ethanone. The preparation method comprises the following steps: carrying out reaction on 2-fluorophenylacetate and cyclopropane carbonyl chloride to prepare cyclopropyl-2-(2-fluorophenyl) ethanone; and then, carrying out halogenating reaction with a bromination reagent to prepare cyclopropyl-2-bromo-2-(2-fluorophenyl) ethanone. The preparation method provided by the invention is carried out under a relatively mild condition, raw materials are easily available, and the obtained product is high in purity and relatively high in yield which reaches over 70%, so that the preparation method is suitable for industrial production.

PROCESS FOR THE PREPARATION OF HIGH-PURITY PRASUGREL

The field of invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of high-purity 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7- tetrahydrothieno[3,2-c]pyridine-2-yl acetate, prasugrel, of Formula (I). Especially in large-scale production, one of the main causes of piling up the impurities is the use of ether solvents consequently in each step in this procedure ethers are excluded. Avoiding the ethers resulted new conditions for production of intermediates in the different steps of our procedure. Conditions were determined so that each step from the beginning contributes to minimizing the impurity content of the end-product.

Method for preparing antithrombotic drug prasugrel intermediate

The invention discloses a method for preparing an antithrombotic drug prasugrel intermediate. The method includes the following steps that firstly, fluorobenzene makes contact and reacts with 1-bromine-3-alkene-diacetyl to generate 1-(2-fluoro-phenyl)-3-alkene-diacetyl under catalysis of Lewis acid, wherein Lewis acid is stannic chloride; secondly, 1-(2-fluoro-phenyl)-3-alkene-diacetyl generated by 1-bromine-3-alkene-diacetyl reacts with dimethyl phosphite methyl sulfonium or dimethyl sulfoxonium methylide to generate 1-cyclopropyl-2-(2-fluoro-phenyl)-2-ethanone; thirdly, 1-cyclopropyl-2-(2-fluoro-phenyl)-2-ethanone obtained in the second step reacts with a bromide reagent to generate the prasugrel intermediate, namely 1-cyclopropyl-2 bromine-2-(2-fluoro-phenyl)-2-ethanone. A brand-new technology is provided for the prasugrel intermediate and synthesis of the prasugrel intermediate, cost is low, the yield is high, processing is easy, and the method is suitable for industrial production.

An anti-platelet drug prasugrel method for the preparation of (by machine translation)

The invention discloses an anti-platelet drug prasugrel method for preparing, the method includes: 1) the 1 [...] cyclopropyl -2 the [...] (the 2 [...] phenyl) - 2 the and iodine monobromide[...] ethanone and the 1 [...] butyl -3 the imidazolium methyl bromination[...] contact is obtained by reacting the 1 [...] cyclopropyl -2 the- [...] the 2 [...] (the 2 [...] phenyl) - 2 the [...] ethanone; 2) and in iodine under the presence of alkali, the step 1) product with the 2 [...] oxo -2, 4, 5, 6, 7 the [...] the 7a [...] tetrahydro-thieno [3,2 the ??c] pyridine hydrochloride is obtained by reacting the 5 [...] (α-cyclopropane carbonyl -2 the [...] fluorobenzyl) - 2 the [...] oxo -2, 4, 5, 6, 7, 7a-tetrahydro-thieno [3,2 the ??c] pyridine; 3) steps 2) product with triethylamine mixed, then instillment second grade anhydride, shall prasugrel stirring reaction. The method of preparing the prasugrel of this invention high yield, is easy to be treated, is suitable for industrial production. (by machine translation)

IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL AND INTERMEDIATE THEREOF

The invention relates to an industrial scale process for the preparation of l-cyclopropyl-2-(2- fluorophenyl)-ethanone of the Formula (1) and the use of this compound for the preparation of prasugrel.

PROCESS FOR PREPARING PRASUGREL

The present invention is directed to an improved process for preparing, prasugrel and maleate salt of Prasugrel and, optionally other pharmaceutically acceptable salts from, prasugrel and said maleate salt, in high yields and purity, which can be used at industrial scale. The process of the present invention comprises the steps of bromination, condensation, acetylating and optionally converting into maleate salt and, if desired, conversion into another pharmaceutically acceptable salt from it. The present process is advantageous in terms of productivity, efficacy, purity and also prevents the use of toxic substances.

Processes For Preparing Prasugrel And Pharmaceutically Acceptable Salts Thereof

Disclosed are improved processes for preparing prasugrel compound of formula-(1), its intermediates and pharmaceutically acceptable salts.

AN IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL HYDROCHLORIDE AND ITS INTERMEDIATES

The present invention provides an improved process for the preparation of prasugrel and its pharmaceutical acceptable salt. Prasugrel chemically known as 2-acetoxy-5-(a- cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine or 5-[2- cyclopropyl-l-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2,-c]pyridine- 2yl acetate and having the structural formula (I) and its pharmaceutically acceptable salts. The present invention also provides an improved process for the preparation of cyclopropyl 2-fluorobenzyl ketone, 2-Fluoro-a-cyclopropyl carbonylbenzyl bromide, 5,6,7,7a Tetrahydro-4H- theino-[3,2-c]- pyridone-2 p-toluenesulfonate and its hydrochloride salt.

METHOD FOR PREPARING PHARMACEUTICALLY ACTIVE INGREDIENT AND INTERMEDIATES THEREOF

The present invention is related to a safe and industrially applicable method for the preparation of 2-acetoxy-5-(2-fluoro-α-cyclopropyl- carbonyl-benzyl)-4,5,6,7-tetrahydro-4H-thieno[3,2-c]pyridine in a quality suitable for use as pharmaceutically active ingredient wherein the concentration of the impurities of the Formula.(XXIV) or (XXIVa) is reduced.

PRASUGREL HYDROCHLORIDE CRYSTALLINE PARTICLES

The present invention relates to prasugrel hydrochloride crystalline particles having mean particle size of more than about 10 μm, to the methods for the manufacture of said crystalline particles, and to pharmaceutical compositions comprising said crystalline particles.