(4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine

Base Information

Chemical Name:(4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine
CAS No.:1379806-97-9
Molecular Formula:C₂₁H₂₀ClFN₂O₃
Molecular Weight:402.853
Hs Code.:

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Chemical Property of (4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine

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Technology Process of (4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine

There total 4 articles about (4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine 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: 15.0%

: 8′-bromo-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano[4,3-b]chromen]-2-amine

: 328956-61-2
3-fluoro-5-chlorophenylboronic acid

: 1379806-97-9
(4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 90 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jm401635n

Reference yield: 15.0%

: 1379806-97-9
(4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine

Guidance literature:

Reference yield:

: 8-bromo-4a-methyl-10-methylene-1,3,4,4a,10,10a-hexahydropyrano[4,3-b]chromene

: 1379806-97-9
(4R,4a′S,10a′S)-8′-(3-chloro-5-fluorophenyl)-4a′-methyl-3′,4′,4a′,10a′-tetrahydro-1′H,5H-spiro[oxazole-4,10′-pyrano-[4,3-b]chromen]-2-amine

Guidance literature:: Multi-step reaction with 3 steps

1: iodine / acetonitrile; ethyl acetate / 1.08 h / 0 - 40 °C

2: ammonium hydroxide / tetrahydrofuran; water / 1 h / 40 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 4 h / 90 °C / Inert atmosphere

With ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; acetonitrile; 3: |Suzuki Coupling;
DOI:10.1021/jm401635n