Reaktion #168260

Reaktionsgleichung

4-(6-chloro-5-cyano-4-(methylthio)pyridin-2-yl)benzoic acid

6-methoxynaphthalen-2-ylboronic acid

potassium phosphate

→

4-(5-cyano-6-(6-methoxynaphthalen-2-yl)-4-(methylthio)pyridin-2-yl)benzoic acid

Ausbeute 64.3%

Lösungsmittel

N,N-dimethylacetamide

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with saturated NH4Cl (5 mL), water (5 ml), brine (5 mL)
2. 2
   Trocknendried (MgSO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was triturated with MeOH (10 ml)
5. 5
   Filtrationfiltered
6. 6
   SonstigeThe yellow solid was collected
7. 7
   Sonstigedried under vacuum

Vorschrift

A mixture of 4-(6-chloro-5-cyano-4-(methylthio)pyridin-2-yl)benzoic acid (50 mg, 0.164 mmol) and 6-methoxynaphthalen-2-ylboronic acid (49.7 mg, 0.246 mmol), potassium phosphate (139 mg, 0.656 mmol) and palladium tetrakis(triphenylphosphine) (18.96 mg, 0.016 mmol) in N,N-dimethylacetamide (2 mL) was pumped under vacuum and backfilled with nitrogen three times. After 2 h at 100° C., the mixture was cooled to room temperature, diluted with EtOAc (60 mL), washed with saturated NH4Cl (5 mL), water (5 ml), brine (5 mL), dried (MgSO4) and concentrated. The residue was triturated with MeOH (10 ml) and filtered. The yellow solid was collected and dried under vacuum to give 4-(5-cyano-6-(6-methoxynaphthalen-2-yl)-4-(methylthio)pyridin-2-yl)benzoic acid (45 mg, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.34-8.53 (2H, m), 8.21-8.34 (1H, m), 7.99-8.19 (4H, m), 7.85-7.98 (1H, m), 7.41-7.54 (1H, m), 7.18-7.37 (2H, m), 3.94 (3H, s); MS (ES+) m/z: 427 (M+H); LC retention time: 4.01 min (analytical HPLC Method A).

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