5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → 6,2'-Difluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-carbonitrile

HRID 1061819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061819
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2.[F:16][C:17]1[C:22]([C:23]2[CH:28]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=[CH:25][C:24]=2[F:38])=[CH:21][C:20]([C:39]#[N:40])=[CH:19][CH:18]=1>>[F:16][C:17]1[C:22]([C:23]2[CH:28]=[C:27]([C:2]3[C:3]4[C:8](=[N:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:26]=[CH:25][C:24]=2[F:38])=[CH:21][C:20]([C:39]#[N:40])=[CH:19][CH:18]=1

Komponenten

3

Edukt 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853016,2'-Difluoro-5'-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-3-carbonitrile

Produkt 1

HCID 101585256,2'-Difluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-carbonitrileAusbeute 27 %

Versuchsvorschrift

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 6,2′-difluoro-5′-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-3-carbonitrile (96 mg, 0.28 mmol) as described in Example 7 part g), affording 6,2′-difluoro-5′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-carbonitrile (24 mg, 27%). δH (400 MHz, CDCl3) 7.35 (1H, t, J 9.0), 7.45 (1H, t, J 9.0), 7.52-7.61 (3H, m), 7.74-7.78 (1H, m), 7.83 (1H, dd, J 1.4 and 6.5), 7.87 (1H, d, J 8.6), 8.54 (1H, d, J 8.2), 9.30 (1H, d, J 4.3). m/z (ES) 412 [MH]+.

Quellen und Nachweise

ORD-Eintrag
ord-ea288886359e43ebb790636e458a1ef5
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960598B2

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