Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate

Base Information

• Chemical Name: Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate
• CAS No.: 272789-54-5
• Molecular Formula: C₂₉H₃₁F₂N₂O₅P
• Molecular Weight: 556.546

Synonyms:Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate

Chemical Property of Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate

There total 7 articles about Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

acetone (67-64-1) + Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-nitrobenzyl}-1,1-difluoromethyl)-phenylphosphinate (272789-49-8) → Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-54-5)

Guidance literature:

With hydrogen; magnesium sulfate; palladium on activated charcoal; In methanol; at 20 ℃; for 120h;

DOI:10.1002/(SICI)1521-3765(20000317)6:6<1050::AID-CHEM1050>3.0.CO;2-5

Reference yield:

2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7) → Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-54-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / K₂CO₃ / acetonitrile / 80 °C

2.1: 87 percent / NaBH₄ / tetrahydrofuran / 0 °C

3.1: 60 percent / PPh₃Br₂ / CH₂Cl₂ / 1 h / 20 °C

4.1: 99 percent / toluene / 18 h / Heating

5.1: NaHMDS / tetrahydrofuran / 0.25 h / -80 °C

5.2: 35 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -80 - 20 °C

6.1: 99 percent / H₂; MgSO₄ / 10 percent Pd/C / methanol / 120 h / 20 °C

With sodium tetrahydroborate; hydrogen; sodium hexamethyldisilazane; magnesium sulfate; potassium carbonate; dibromotriphenylphosphorane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1.1: Etherification / 2.1: Reduction / 3.1: Substitution / 4.1: Michaelis-Arbuzov condensation / 5.1: Metallation / 5.2: Fluorination / 6.1: Reduction;

DOI:10.1002/(SICI)1521-3765(20000317)6:6<1050::AID-CHEM1050>3.0.CO;2-5

Reference yield:

2-nitro-5-hydroxybenzaldehyde (42454-06-8) → Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-54-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / K₂CO₃ / acetonitrile / 80 °C

2.1: 87 percent / NaBH₄ / tetrahydrofuran / 0 °C

3.1: 60 percent / PPh₃Br₂ / CH₂Cl₂ / 1 h / 20 °C

4.1: 99 percent / toluene / 18 h / Heating

5.1: NaHMDS / tetrahydrofuran / 0.25 h / -80 °C

5.2: 35 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -80 - 20 °C

6.1: 99 percent / H₂; MgSO₄ / 10 percent Pd/C / methanol / 120 h / 20 °C

With sodium tetrahydroborate; hydrogen; sodium hexamethyldisilazane; magnesium sulfate; potassium carbonate; dibromotriphenylphosphorane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1.1: Etherification / 2.1: Reduction / 3.1: Substitution / 4.1: Michaelis-Arbuzov condensation / 5.1: Metallation / 5.2: Fluorination / 6.1: Reduction;

DOI:10.1002/(SICI)1521-3765(20000317)6:6<1050::AID-CHEM1050>3.0.CO;2-5

upstream raw materials:

acetone

Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-nitrobenzyl}-1,1-difluoromethyl)-phenylphosphinate

2-(3-bromopropyl)isoindole-1,3-dione

2-nitro-5-hydroxybenzaldehyde

Downstream raw materials:

Ethyl {1-[5-(3-aminopropoxy)-2-(isopropylmethylamino)-phenyl]-1,1-difluoromethyl}-phenylphosphinate

Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-(isopropylmethylamino)-phenyl}-1,1-difluoromethyl)-phenylphosphinate

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