3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide

Base Information

• Chemical Name: 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide
• CAS No.: 1346133-11-6
• Molecular Formula: C₂₄H₂₂F₂N₂O₂
• Molecular Weight: 408.448

Synonyms:3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide

Chemical Property of 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

LY2444296 ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

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Technology Process of 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide

There total 10 articles about 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide 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: 46.0%

3-fluoro-4-(4-formylphenoxy)benzamide (676494-56-7) + (2S)-2-(3-fluorophenyl)pyrrolidine (920274-04-0,920274-03-9) → 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide (1346133-11-6)

Guidance literature:

3-fluoro-4-(4-formylphenoxy)benzamide; (2S)-2-(3-fluorophenyl)pyrrolidine; In 1,2-dichloro-ethane; at 20 ℃; for 20h; Molecular sieve;

With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 3h;

DOI:10.1021/acs.orglett.7b01828

Reference yield:

3-fluorobromobenzene (1073-06-9) → 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide (1346133-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium; iodine / tetrahydrofuran / Reflux

1.2: 2 h / -78 °C / Inert atmosphere; Schlenk technique; Glovebox

2.1: trifluoroacetic acid / tetrahydrofuran / 1 h / Inert atmosphere; Schlenk technique; Glovebox

2.2: 10 h / 30 °C / 7600.51 Torr / Autoclave

3.1: 1,2-dichloro-ethane / 20 h / 20 °C / Molecular sieve

3.2: 3 h / 20 °C

With iodine; magnesium; trifluoroacetic acid; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.7b01828

Reference yield:

tert-butyl (4-(3-fluorophenyl)-4-oxobutyl)carbamate (1223405-24-0) → 3-fluoro-4-[4-[[ (2S)-2-(3-fluorophenyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide (1346133-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / tetrahydrofuran / 1 h / Inert atmosphere; Schlenk technique; Glovebox

1.2: 10 h / 30 °C / 7600.51 Torr / Autoclave

2.1: 1,2-dichloro-ethane / 20 h / 20 °C / Molecular sieve

2.2: 3 h / 20 °C

With trifluoroacetic acid; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.7b01828

upstream raw materials:

3-fluoro-4-(4-formylphenoxy)benzonitrile

3-fluoro-4-(4-formylphenoxy)benzamide

(2S)-2-(3-fluorophenyl)pyrrolidine

3,4-Difluorobenzonitrile

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