2-(3-Methyoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine synthesis

4synthesis methods

Product Name:2-(3-Methyoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
CAS Number:1159803-56-1
Molecular formula:C17H15BN2O
Molecular Weight:274.12

1214264-88-6 Synthesis

1-pinacolato-2-(1,8)diamo-naphthalenylborane

1214264-88-6
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536-90-3 Synthesis

536-90-3
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2-(3-Methyoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

1159803-56-1
15 suppliers
$75.00/500mg

Yield:1159803-56-1 70%

Reaction Conditions:

with tert.-butylnitrite;sodium acetate;tetra-(n-butyl)ammonium iodide;dibenzoyl peroxide in acetonitrile at 80;Schlenk technique;Inert atmosphere;

Steps:

4.2. General Procedure for the Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides

General procedure: In air, Bpin-B(dan) (0.1 mmol, 1.0 eq.), aryl amide (0.2 mmol, 2.0 eq.), TBAI (0.01 eq.),NaOAc (0.15 eq.), and BPO (0.01 eq.) were sequentially weighed and added to a screw-cappedSchenk tube containing a magnetic stir bar. The vessel was evacuated and refilled with nitrogen forthree times. t-BuONO (0.2 eq.) and MeCN (0.6 mL) were added in turn under N2 atmosphere usingsyringes through a septum which was temporarily used to replace the screw cap. The reaction mixturewas then vigorously stirred at 80 °C for the indicated time. The resulting mixture was filtered through a pad of Celite, and the filter cake was washed with ethyl acetate (3 mL x 2). The combined filtratewas evaporated under vacuum to dryness and the residue was purified by column chromatography toyield the desired product.

References:

Ding, Siyi;Ma, Qiang;Zhu, Min;Ren, Huaping;Tian, Shaopeng;Zhao, Yuzhen;Miao, Zongcheng [Molecules,2019,vol. 24,# 3,art. no. 377]

2398-37-0 Synthesis