(4-Amino-3'-chloro-biphenyl-3-yl)-propynyl-methanone → (4-Amino-3'-chloro-biphenyl-3-yl)-dipropynyl-methanol

HRID 413146

Reaktionsgleichung

Reaktionsgleichung von HRID 413146
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([C:17]#[C:18][CH3:19])=[O:16].[C:20]([Mg]Br)#[C:21][CH3:22]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([C:20]#[C:21][CH3:22])([C:17]#[C:18][CH3:19])[OH:16]

Komponenten

3

Edukt 2

HCID 23509596(4-Amino-3'-chloro-biphenyl-3-yl)-propynyl-methanoneHCID 178419101HCID 178419101, Verbindung

Produkt 1

HCID 22736629(4-Amino-3'-chloro-biphenyl-3-yl)-dipropynyl-methanol

Versuchsvorschrift

Following the procedure of Example 41, (4-amino-3′-chloro-biphenyl-3-yl)-propynyl-methanone (mp 112-114° C.; MS ((+) ESI) m/z 270/272 (M+H)+) was treated with propynylmagnesium bromide to give (4-amino-3′-chloro-biphenyl-3-yl)-dipropynyl-methanol which was reacted with 1,1′-carbonyldiimidazole to afford the title compound. Yellow solid: mp 151° C. (decomposed); 1H-NMR (DMSO-d6) δ10.8 (s, 1H), 7.71 (dd, 1H, J=8.52,1.94 Hz), 7.69 (m, 2H), 7.61 (d, 1H, J=7.64 Hz), 7.50 (t, 1H, J=7.85 Hz), 7.43 (d, 1H, J=7.99 Hz), 7.06 (d, 1H, J=8.23 Hz), 2.0 (s, 6H); MS (APCI) m/z 336 ([M+H]+, 20%).

Quellen und Nachweise

ORD-Eintrag
ord-8d3b24a94f9444269abd7ca3ac1276c0
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566358B2

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