(S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide

Base Information

• Chemical Name: (S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide
• CAS No.: 875714-51-5
• Molecular Formula: C₁₇H₁₉BrN₂OS
• Molecular Weight: 379.321

Synonyms:(S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide

Chemical Property of (S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide

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Technology Process of (S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide

There total 1 articles about (S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide 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: 41.0%

1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-one (127049-48-3) + (S)-p-toluenesulfinimide (188447-91-8) → (SS)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide (875714-51-5)

Guidance literature:

With titanium(IV) tetraethanolate; In tetrahydrofuran; at 70 ℃; for 36h;

DOI:10.1016/j.tet.2005.10.011

Reference yield:

(SS)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide (875714-51-5) → (SS,R)-N-(2,2-dimethyl-1-(pyridin-2-yl)propyl)-4-methylbenzenesulfinamide + (SS,S)-N-(2,2-dimethyl-1-(pyridin-2-yl)propyl)-4-methylbenzenesulfinamide

Guidance literature:

(S_S)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide; With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 6h;

With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; at 20 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2005.10.011

Reference yield:

(SS)-N-(1-(6-bromopyridin-2-yl)-2,2-dimethylpropylidene)-4-methylbenzenesulfinamide (875714-51-5) → (SS,R)-N-[2,2-dimethyl-1-(6-morpholinopyridin-2-yl)propyl]-4-methylbenzenesulfinamide

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / diisobutylaluminium hydride / tetrahydrofuran / 6 h / -78 °C

2: 93 percent / 1,3-bis(diphenylphosphino)propane; NaO-t-Bu / Pd₂(dba)3 / toluene / 9 h / 70 °C

With 1,3-bis-(diphenylphosphino)propane; diisobutylaluminium hydride; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; toluene;

DOI:10.1016/j.tet.2005.10.011

upstream raw materials:

1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-one

(S)-p-toluenesulfinimide

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