5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

Base Information

Chemical Name:5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid
CAS No.:936476-86-7
Molecular Formula:C₂₅H₂₈N₂O₄S
Molecular Weight:452.574
Hs Code.:

5-{5-[2-(<i>tert</i>-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

Synonyms:5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

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Chemical Property of 5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

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Technology Process of 5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

There total 7 articles about 5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid 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: 100.0%

: 928260-43-9
5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid ethyl ester

: 936476-86-7
5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

Guidance literature:: With potassium trimethylsilonate; In tetrahydrofuran; for 18h;
DOI:10.1016/j.bmcl.2006.10.045

Reference yield:

: 144873-99-4
(6-bromopyridine-3-yl)acetonitrile

: 936476-86-7
5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 80 °C

2: 90 percent / H₂ / Raney Ni / ethanol; tetrahydrofuran / 18 h

3: methanol / 3 h

4: NaBH₄ / 1 h

5: 80 percent / i-Pr₂NEt / CH₂Cl₂

6: 100 percent / KOTMS / tetrahydrofuran / 18 h

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium trimethylsilonate; hydrogen; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Negishi coupling;
DOI:10.1016/j.bmcl.2006.10.045

Reference yield:

: 352530-37-1
5-(ethoxycarbonyl)thiophene-2-ylzinc bromide

: 936476-86-7
5-{5-[2-(tert-butoxycarbonyl-phenethyl-amino)-ethyl]-pyridin-2-yl}-thiophene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 80 °C

2: 90 percent / H₂ / Raney Ni / ethanol; tetrahydrofuran / 18 h

3: methanol / 3 h

4: NaBH₄ / 1 h

5: 80 percent / i-Pr₂NEt / CH₂Cl₂

6: 100 percent / KOTMS / tetrahydrofuran / 18 h

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium trimethylsilonate; hydrogen; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Negishi coupling;
DOI:10.1016/j.bmcl.2006.10.045