1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone

Base Information

• Chemical Name: 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone
• CAS No.: 1449135-16-3
• Molecular Formula: C₁₈H₁₄ClFN₂O₂
• Molecular Weight: 344.773

Synonyms:1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone

Chemical Property of 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone

Chemical Property:

Purity/Quality:

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Technology Process of 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone

There total 4 articles about 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone 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: 79.0%

N-((1-acetyl-1H-indol-2-yl)methyl)-4-fluorobenzamide (1449135-30-1) → 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone (1449135-16-3)

Guidance literature:

With 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; 1,3-dichloro-5,5-diphenylhydantoin; In dichloromethane; at -30 ℃; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol4020943

Reference yield:

1-(1H-indol-2-yl)methanamine (21109-25-1) → 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone (1449135-16-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: 1,3-dichloro-5,5-diphenylhydantoin; 1,4-bis-(9-O-dihydroquinidinyl)phthalazine / dichloromethane / -30 °C / Inert atmosphere; Schlenk technique

With 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; 1,3-dichloro-5,5-diphenylhydantoin; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol4020943

Reference yield:

4-fluorobenzoyl chloride (403-43-0) → 1-((2R,3S)-3-chloro-2'-(4-fluorophenyl)-4'H-spiro[indoline-2,5'-oxazol]-1-yl)ethanone (1449135-16-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: 1,3-dichloro-5,5-diphenylhydantoin; 1,4-bis-(9-O-dihydroquinidinyl)phthalazine / dichloromethane / -30 °C / Inert atmosphere; Schlenk technique

With 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; 1,3-dichloro-5,5-diphenylhydantoin; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol4020943

upstream raw materials:

N-((1-acetyl-1H-indol-2-yl)methyl)-4-fluorobenzamide

4-fluorobenzoyl chloride

2-(4-fluorobenzoylaminomethyl)indole

1-(1H-indol-2-yl)methanamine

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