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

Base Information

• Chemical Name: Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-(isopropylmethylamino)-phenyl}-1,1-difluoromethyl)-phenylphosphinate
• CAS No.: 272789-55-6
• Molecular Formula: C₃₀H₃₃F₂N₂O₅P
• Molecular Weight: 570.573

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-(isopropylmethylamino)-phenyl}-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: 97.0%

Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-isopropylaminophenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-54-5) + methyl iodide (74-88-4) → Ethyl (1-{5-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propoxy]-2-(isopropylmethylamino)-phenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-55-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 48h;

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-(isopropylmethylamino)-phenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-55-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: 97 percent / K₂CO₃ / acetonitrile / 48 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 / 7.1: Methylation;

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-(isopropylmethylamino)-phenyl}-1,1-difluoromethyl)-phenylphosphinate (272789-55-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: 97 percent / K₂CO₃ / acetonitrile / 48 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 / 7.1: Methylation;

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

upstream raw materials:

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

methyl iodide

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

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