4-Iodoanisole → N-([1,1'-biphenyl]-4-yl)-N-(4-methoxyphenyl)-[1,1':3',1''-terphenyl]-4'-amine

Toluene (200 mL) was bubbled with nitrogen for 15 min, followed by addition of 10% t-Bu3P in hexane (2.9 mL, 1.0 mmol) and Pd2(dba)3 (1.1 g, 1.2 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′:3′,1″-terphenyl]-4′-amine (10.6 g, 26.5 mmol), 4-iodoanisole (11.2 g, 48.0 mmol), sodium tert-butoxide (3.5 g, 36.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and stirred for 16 h at room temperature. The reaction mixture was filtered through a silica pad and washed with toluene (containing 0.5% triethylamine). The solvent was removed in vacuo and the residue was purified by flash chromatography using 30-40% toluene/hexane (containing 0.5% triethylamine) to afford N-([1,1′-biphenyl]-4-yl)-N-(4-methoxyphenyl)-[1,1′:3′,1″-terphenyl]-4′-amine (12.5 g, 94% yield) as a white solid.

1. customToluene (200 mL) was bubbled with nitrogen for 15 min
2. customThe mixture was bubbled with nitrogen for 15 min
3. customThe mixture was bubbled with nitrogen for 15 min
4. filtrationThe reaction mixture was filtered through a silica pad
5. washwashed with toluene (containing 0.5% triethylamine)
6. customThe solvent was removed in vacuo
7. customthe residue was purified by flash chromatography

ORD-Eintrag

ord-2f8558c126e34378bcd9258097a7ffb4

Quelldatensatz

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08716484B1