Reaktion #2443983

Reaktionsgleichung

bis(pinacolato)diboron

methyl 4-bromo-2-methylbenzoate

KOAc

N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amine

NaHCO3

→

methyl 3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methylbiphenyl-4-carboxylate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAs shown in Reaction Scheme 6
2. 2
   Sonstigewas degassed with argon for 30 min at rt
3. 3
   TemperaturAfter cooling the mixture to rt
4. 4
   TemperaturThe mixture was heated at 85° C. overnight
5. 5
   Extraktionextracted with EtOAc
6. 6
   TrocknenThe combined organic phases were dried over Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigepurified by column chromatography (20% EtOAc in hexanes)

Vorschrift

As shown in Reaction Scheme 6, a mixture of bis(pinacolato)diboron (0.55 g, 2.2 mmol), methyl 4-bromo-2-methylbenzoate (0.50 g, 2.2 mmol), palladium(II) acetate (0.01 g, 0.07 mmol), and KOAc (0.64 g, 6.6 mmol) in DMF (7.5 mL) was degassed with argon for 30 min at rt. The mixture was then heated at 80° C. for 4 h. After cooling the mixture to rt, N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amine (0.74 g, 2.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.08 g, 0.07 mmol), and saturated aqueous NaHCO3 (5 mL) were added. The mixture was heated at 85° C. overnight. The mixture was poured into ice water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (20% EtOAc in hexanes). This yielded 0.345 g (39%) of the title compound. LC/MS m/z 411.3 (MH+; retention time 4.15 min. 1H NMR (400 MHz, CD2Cl2) 2.62 (s, 3H), 3.90 (s, 3H), 7.10 (t, 1H), 7.39-7.53 (m, 5H), 7.62-7.70 (m, 1H), 7.99 (d, 1H), 8.58 (t, 1H).

Quelle