1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

Base Information

Chemical Name:1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one
CAS No.:889878-50-6
Molecular Formula:C₂₇H₂₃FN₂O₂
Molecular Weight:426.49
Hs Code.:

Synonyms:1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

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Chemical Property of 1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

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Technology Process of 1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

There total 11 articles about 1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one 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: 76.0%

: 889878-49-3
1-(4-fluoro-phenyl)-3-isopropyl-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-2-carbaldehyde

: 889878-50-6
1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

Guidance literature:: 1-(4-fluoro-phenyl)-3-isopropyl-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-2-carbaldehyde; With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

With water; sodium hydrogencarbonate; In tetrahydrofuran; ethyl acetate;

Reference yield:

: 889878-44-8
3-(2-bromo-phenyl)-4-(4-fluoro-phenyl)-1H-pyrrole-2-carboxylic acid ethyl ester

: 889878-50-6
1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: KOH / dimethylsulfoxide / 2 h / 25 °C

2: POCl₃ / 1,2-dichloro-ethane / 18 h / 80 °C

3: NaOH / methanol / 3 h / 60 °C

4: SOCl₂ / 1 h / 70 °C

5: Et₃N / CH₂Cl₂ / 12 h / 0 - 25 °C

6: 37 percent / [9,9-dimethyl-4,5-bis(diphenylphosphino)]xanthane; Cs₂CO₃ / Pd(OAc)2 / toluene / 16 h / 100 °C

7: 49 percent / LiAl(O-t-Bu)3H / tetrahydrofuran / 0.5 h / 0 °C

With potassium hydroxide; sodium hydroxide; thionyl chloride; caesium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; trichlorophosphate; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene; 2: Vilsmeier-Haack formylation / 6: Buchwald aryl-amidation;
DOI:10.1016/j.bmcl.2007.05.097

Reference yield:

: 889878-45-9
3-(2-bromo-phenyl)-4-(4-fluoro-phenyl)-1-isopropyl-1H-pyrrole-2-carboxylic acid ethyl ester

: 889878-50-6
1-(4-fluoro-phenyl)-2-hydroxymethyl-3-isopropyl-5-phenyl-3,5-dihydro-pyrrolo[2,3-c]quinolin-4-one

Guidance literature:: Multi-step reaction with 6 steps

1: POCl₃ / 1,2-dichloro-ethane / 18 h / 80 °C

2: NaOH / methanol / 3 h / 60 °C

3: SOCl₂ / 1 h / 70 °C

4: Et₃N / CH₂Cl₂ / 12 h / 0 - 25 °C

5: 37 percent / [9,9-dimethyl-4,5-bis(diphenylphosphino)]xanthane; Cs₂CO₃ / Pd(OAc)2 / toluene / 16 h / 100 °C

6: 49 percent / LiAl(O-t-Bu)3H / tetrahydrofuran / 0.5 h / 0 °C

With sodium hydroxide; thionyl chloride; caesium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; trichlorophosphate; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene; 1: Vilsmeier-Haack formylation / 5: Buchwald aryl-amidation;
DOI:10.1016/j.bmcl.2007.05.097