[(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate
• CAS No.: 943025-77-2
• Molecular Formula: C₁₈H₁₅FN₂O₅S
• Molecular Weight: 390.392
• Mol file: 943025-77-2.mol

Synonyms:[(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

Chemical Property of [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

There total 5 articles about [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate 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:

(4R/S)-3-fluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (943025-64-7) + p-toluenesulfonyl chloride (98-59-9) → [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate (943025-77-2)

Guidance literature:

With triethylamine; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 18h; Product distribution / selectivity;

Reference yield:

8-bromo-7-fluoro-2-methoxy-1,5-naphthyridine (724788-70-9) → [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate (943025-77-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 0.5 h / 20 °C

1.2: 10 h / Reflux

2.1: cerium(III) chloride heptahydrate; sodium hypochlorite / tert-butyl alcohol / 0.5 h / 20 °C

3.1: sodium iodide / acetone / 18 h / Reflux

4.1: / water; tert-butyl alcohol / 16 h / 20 °C

5.1: di(n-butyl)tin oxide; triethylamine / dichloromethane; tetrahydrofuran; N,N-dimethyl-d₆-formamide / 18 h / 20 °C

With sodium hypochlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; di(n-butyl)tin oxide; triethylamine; sodium iodide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; acetone; N,N-dimethyl-d₆-formamide; tert-butyl alcohol; 1.1: |Suzuki Coupling / 1.2: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.07.013

Reference yield:

7-fluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine (943025-69-2) → [(4R/S)-3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate (943025-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: cerium(III) chloride heptahydrate; sodium hypochlorite / tert-butyl alcohol / 0.5 h / 20 °C

2: sodium iodide / acetone / 18 h / Reflux

3: / water; tert-butyl alcohol / 16 h / 20 °C

4: di(n-butyl)tin oxide; triethylamine / dichloromethane; tetrahydrofuran; N,N-dimethyl-d₆-formamide / 18 h / 20 °C

With sodium hypochlorite; cerium(III) chloride heptahydrate; di(n-butyl)tin oxide; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; acetone; N,N-dimethyl-d₆-formamide; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2013.07.013

upstream raw materials:

(4R/S)-3-fluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

p-toluenesulfonyl chloride

8-bromo-7-fluoro-2-methoxy-1,5-naphthyridine

7-fluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine