(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

Base Information

Chemical Name:(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate
CAS No.:1339751-88-0
Molecular Formula:C₂₁H₂₁BN₂O₃
Molecular Weight:360.22
Hs Code.:

Synonyms:(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

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Chemical Property of (S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

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Technology Process of (S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

There total 3 articles about (S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate 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:

: 1393880-53-9
(E)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)acrylate

: 1339751-88-0
(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

: 1393880-61-9
(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

Guidance literature:: With (R)-tol-BINAP; copper(l) chloride; sodium t-butanolate; In toluene; at 20 ℃; for 0.333333h; Overall yield = 77 %; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ol301958x

Reference yield:

: 104-92-7
1-bromo-4-methoxy-benzene

: 1339751-51-7
methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

: 1339751-88-0
(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

Guidance literature:: methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate; With potassium hydrogenfluoride; In acetonitrile;

1-bromo-4-methoxy-benzene; With palladium diacetate; potassium carbonate; XPhos; In water; toluene; at 80 ℃; for 6h; chemoselective reaction;
DOI:10.1038/nchem.1150

Reference yield:

: 696-62-8
para-iodoanisole

: CH₃OCOCHCHB(NHC₁₀H₆NH)

: 1339751-88-0
(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

: 1393880-61-9
(S)-methyl 3-(4-methoxyphenyl)-3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)propanoate

Guidance literature:: Multi-step reaction with 2 steps

1: palladium diacetate; triphenylphosphine; triethylamine; tetra(n-butyl)ammonium hydrogensulfate / acetonitrile / 10 h / 80 °C / Inert atmosphere

2: copper(l) chloride; (R)-tol-BINAP; sodium t-butanolate / toluene / 0.33 h / 20 °C / Inert atmosphere

With tetra(n-butyl)ammonium hydrogensulfate; palladium diacetate; (R)-tol-BINAP; triethylamine; triphenylphosphine; copper(l) chloride; sodium t-butanolate; In toluene; acetonitrile; 1: |Heck Reaction;
DOI:10.1021/ol301958x