trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Base Information

Chemical Name:trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide
CAS No.:951655-79-1
Molecular Formula:C₂₃H₂₂N₂O₄
Molecular Weight:390.439
Hs Code.:

Synonyms:trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

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Chemical Property of trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

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Technology Process of trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

There total 8 articles about trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide 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: 72.0%

: 951655-73-5
trans-3-[3-(1H-indole-2-carbonyl)phenyl]acrylic acid

: 6723-30-4
O-2-tetrahydro-2H-pyranhydroxylamine

: 951655-79-1
trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jm0703136

Reference yield:

: 773101-97-6
3-[1,3]dioxolan-2-yl-benzoic acid

: 951655-79-1
trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 66 percent / SOCl₂; pyridine / tetrahydrofuran / 0.5 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 36 percent / hexane; tetrahydrofuran / -78 - 20 °C

3.1: 38 percent / aq. HClO₄ / CH₂Cl₂ / 0 °C

4.1: 64 percent / aq. NaOH; NEt₃ / CH₂Cl₂ / 96 h / 20 °C

5.1: 76 percent / TFA / 1 h / 20 °C

6.1: 98 percent / aq. NaOH / methanol / 12 h / Heating

7.1: 72 percent / BOP; NEt₃ / dimethylformamide / 1 h / 20 °C

With pyridine; sodium hydroxide; n-butyllithium; thionyl chloride; perchloric acid; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Wittig olefination;
DOI:10.1021/jm0703136

Reference yield:

: 951655-57-5
3-[1,3]dioxolan-2-ylbenzoyl chloride

: 951655-79-1
trans-3-[3-(1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 36 percent / hexane; tetrahydrofuran / -78 - 20 °C

2.1: 38 percent / aq. HClO₄ / CH₂Cl₂ / 0 °C

3.1: 64 percent / aq. NaOH; NEt₃ / CH₂Cl₂ / 96 h / 20 °C

4.1: 76 percent / TFA / 1 h / 20 °C

5.1: 98 percent / aq. NaOH / methanol / 12 h / Heating

6.1: 72 percent / BOP; NEt₃ / dimethylformamide / 1 h / 20 °C

With sodium hydroxide; n-butyllithium; perchloric acid; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Wittig olefination;
DOI:10.1021/jm0703136