4-Bromo-2-fluorophenylisothiocyanate → Ethyl 2-[(4-bromo-2-fluorophenyl)amino]thieno[2,3-b]pyridine-3-carboxylate

HRID 1944058

Reaktionsgleichung

Reaktionsgleichung von HRID 1944058
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[S:23])=[C:17]([F:24])[CH:16]=1>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[S:23][C:2]3=[N:3][CH:4]=[CH:5][CH:6]=[C:7]3[C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:17]([F:24])[CH:16]=1

Komponenten

3

Edukt 2

HCID 27570034-Bromo-2-fluorophenylisothiocyanateHCID 15326671Ethyl 2-(2-chloropyridin-3-yl)acetate

Produkt 1

HCID 68923401Ethyl 2-[(4-bromo-2-fluorophenyl)amino]thieno[2,3-b]pyridine-3-carboxylate

Versuchsvorschrift

Prepared from ethyl (2-chloropyridin-3-yl)acetate (D. H. Bremner et al., Synthesis, 1997, 949) (500 mg, 2.5 mmol) and 4-bromo-2-fluorophenyl isothiocyanate (580 mg, 2.5 mmol) by the method of Example 1. Title compound obtained as an off-white solid (390 mg, 40%). δH (DMSO-d6) 10.37 (1H, br s), 8.25 (1H, dd, J 1.4, 8.1 Hz), 8.19 (1H, d, J=4.8 Hz), 7.69 (1H, dd, J 1.8, 10.2 Hz), 7.56-7.45 (2H, m), 7.32 (1H, dd, J 4.5, 8.1 Hz), 4.35 (2H, q, J=7.1 Hz), 1.37 (3H, t, J=7.1 Hz). LCMS (ES+) RT 4.66 minutes, 395 (M(79Br)+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-6dc55a984c87430ba96e17243b06acc0
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394822B2

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