Toluene → HCID 59385244, compound

As shown in Reaction Scheme 5, to a mixture of N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amine (1.00 g, 2.93 mmol) and 4-(methoxycarbonylphenyl)boronic acid (0.79 g, 4.40 mmol) in toluene (10 mL) was added Na2CO3 (1.40 g, 13.2 mmol), 1,1′-bis(diphenylphosphino) ferrocenepalladium(II) chloride complex with dichloromethane (0.05 g, 0.06 mmol), 1,4-dioxane (5 mL), and water (5 mL). This mixture was heated at reflux overnight. Upon cooling to rt, the reaction mixture was filtered, and the solid was washed with water (2×30 mL) and methanol (2×30 mL). The solid was recrystallized from acetone/MeOH (2:1). This yielded 0.641 g (55%) of the desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 3.82 (s, 3H), 7.20 (t, 1H), 7.59-8.02 (m, 8H), 8.70 (t, 1H), 10.50 (bs, 1H).

1. temperatureThis mixture was heated
2. temperatureat reflux overnight
3. filtrationthe reaction mixture was filtered
4. washthe solid was washed with water (2×30 mL) and methanol (2×30 mL)
5. customThe solid was recrystallized from acetone/MeOH (2:1)

ORD record

ord-b1059b42da564c0eb250ee7211cf5cda

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759376B2