1-(4-Bromo-2-fluorophenyl)ethan-1-one → 1-(4-Bromo-2-fluorophenyl)ethan-1-amine

HRID 2422878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422878
C([C:4]1[CH:9]=[C:8]([CH:10]([NH2:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])C=C.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[C:25]([F:32])[CH:24]=1>>[F:32][C:9]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[CH:6]=[CH:7][C:8]=1[CH:10]([NH2:12])[CH3:11].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([NH2:12])[CH3:30])=[C:25]([F:32])[CH:24]=1

Komponenten

4

Edukt 2

HCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-oneHCID 67244664HCID 67244664, Verbindung

Produkt 2

HCID 185435761-(4-Bromo-2-fluorophenyl)ethan-1-amineHCID 672458741-(3,5'-Difluoro-2'-methoxy-biphenyl-4-yl)-ethylamine

Versuchsvorschrift

1-(3,5′-Difluoro-2′-methoxy-biphenyl-4-yl)-ethylamine was prepared in a similar manner to 1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (Example 34) using 4′-bromo-2′-fluoroacetophenone to give 1-(4-bromo-2-fluoro-phenyl)-ethylamine. To a solution of 1-(3,5′-difluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (20.0 mg, 0.08 mmol) in dichloromethane (1 ml) was added triethylamine (8.1 mg, 0.08 mmol) and 1-methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonyl chloride (14.2 mg, 0.06 mmol). The solution was stirred overnight then the solvent evaporated and the residue purified by flash chromatography over silica gel eluting with dichloromethane. Evaporation of solvent under reduced pressure gave the title compound (20 mg). 1H NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 7.21-7.16 (m, 2H), 7.14-7.09 (m, 1H), 7.05-6.95 (m, 2H), 6.93-6.88 (m, 1H), 5.11 (d, 1H), 4.76 (dq, 1H), 3.81 (s, 3H), 3.73 (s, 3H), 1.55 (d, 3H) ppm; MS (ESI) m/z: 498.3 [M+Na]+.

Quellen und Nachweise

ORD-Eintrag
ord-b6eda5b5181c43148547b4c99dc4037e
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960365B2

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