nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

Base Information

Chemical Name:nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester
CAS No.:913181-91-6
Molecular Formula:C₂₅H₃₃BN₂O₆
Molecular Weight:468.358
Hs Code.:

nicotinic acid 2-<i>tert</i>-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

Synonyms:nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

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Chemical Property of nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

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Technology Process of nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

There total 5 articles about nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester 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: 73.0%

: 913181-85-8
nicotinic acid 1-(4-bromo-phenyl)-2-tert-butoxycarbonylamino-ethyl ester

: 73183-34-3
bis(pinacol)diborane

: 913181-91-6
nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

Guidance literature:: With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 18h;
DOI:10.1016/j.bmcl.2006.07.043

Reference yield:

: 339185-70-5
1,1-dimethylethyl [2-(4-bromophenyl)-2-oxoethyl]carbamate

: 913181-91-6
nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / sodium borohydride / methanol / 1 h / 20 °C

2: 76 percent / diisopropylethylamine / CH₂Cl₂ / 18 h / 20 °C

3: 73 percent / potassium acetate; palladium diphenylphosphoferrocene dichloride / dimethylsulfoxide / 18 h / 80 °C

With sodium tetrahydroborate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; dimethyl sulfoxide; 3: Miyaura boronylation;
DOI:10.1016/j.bmcl.2006.07.043

Reference yield:

: 913181-90-5
tert-butyl (2-(4-bromophenyl)-2-hydroxyethyl)carbamate

: 913181-91-6
nicotinic acid 2-tert-butoxycarbonylamino-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / diisopropylethylamine / CH₂Cl₂ / 18 h / 20 °C

2: 73 percent / potassium acetate; palladium diphenylphosphoferrocene dichloride / dimethylsulfoxide / 18 h / 80 °C

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; 2: Miyaura boronylation;
DOI:10.1016/j.bmcl.2006.07.043