(S_s)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide

Base Information

• Chemical Name: (S_s)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide
• CAS No.: 915415-68-8
• Molecular Formula: C₃₉H₃₆N₄O₂S
• Molecular Weight: 624.806

Synonyms:(S_s)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide

Chemical Property of (S_s)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide

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Technology Process of (S_s)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide

There total 6 articles about (S_s)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-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: 68.0%

(S)-(+)-N-((1E)-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}methylidene)-4-methylbenzenesulfinamide (915415-67-7) + 3-cyano-4-methylpyridine (5444-01-9) → (Ss)-N-[(1R)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide + (Ss)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide (915415-68-8)

Guidance literature:

3-cyano-4-methylpyridine; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - -76 ℃;

(S)-(+)-N-((1E)-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}methylidene)-4-methylbenzenesulfinamide; In tetrahydrofuran; at -78 ℃; for 0.0333333h;

DOI:10.1021/jo061443+

Reference yield:

1-benzyl-3-(2-(benzyloxy)ethyl)-1H-indole-2-carbaldehyde (915415-65-5) → (Ss)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide (915415-68-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 76 percent / Ti(OEt)4 / CH₂Cl₂ / 20 h / Heating

2.1: NaHMDS / tetrahydrofuran / -78 - -76 °C

2.2: 68 percent / tetrahydrofuran / 0.03 h / -78 °C

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo061443+

Reference yield:

2-(3-indole)-ethanol (526-55-6,930395-07-6) → (Ss)-(-)-N-[(1S)-1-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}-2-(3-cyanopyridin-4-yl)ethyl]-4-methylbenzenesulfinamide (915415-68-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: 95 percent / POCl₃ / 12 h / 60 °C

3.1: 76 percent / Ti(OEt)4 / CH₂Cl₂ / 20 h / Heating

4.1: NaHMDS / tetrahydrofuran / -78 - -76 °C

4.2: 68 percent / tetrahydrofuran / 0.03 h / -78 °C

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; sodium hydride; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: Vilsmeier formylation reaction;

DOI:10.1021/jo061443+

upstream raw materials:

(S)-(+)-N-((1E)-{1-benzyl-3-[2-(benzyloxy)ethyl]-1H-indol-2-yl}methylidene)-4-methylbenzenesulfinamide

3-cyano-4-methylpyridine

1-benzyl-3-(2-(benzyloxy)ethyl)-1H-indole-2-carbaldehyde

2-(3-indole)-ethanol

Downstream raw materials:

3-[1-benzyl-3-(2-benzyloxy-ethyl)-1H-indol-2-yl]-1-methyl-3,4-dihydro-[2,7]naphthyridine

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