Reaktion #797366

Reaktionsgleichung

Intermediate 52

Tert-butyl 4-(2-bromobenzo[d]oxazol-5-yl)piperidine-1-carboxylate

2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

KF

→

titled compound

Ausbeute 6.8%

Tert-butyl 4-[2-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-5-yl]piperidine-1-carboxylate

Ausbeute 6.8%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture was purged with N2 for 30 mins
2. 2
   workup.ADDITIONCH2Cl2 was added to the above mixture
3. 3
   Sonstigeagain purged with N2 for 30 mins
4. 4
   Sonstigefollowed by purification on combiflash
5. 5
   workup.ADDITIONa gradient mixture of EtOAc and Petether (55:45) as eluent

Vorschrift

Intermediate 52 (40 mg, 0.1 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (30 mg, 0.12 mmol) and KF (18 mg, 0.3 mmol) were dissolved in a mixture of DMF (1 ml) and water (0.4 ml). This mixture was purged with N2 for 30 mins. Pd(dppf)Cl2.CH2Cl2 was added to the above mixture and again purged with N2 for 30 mins. This reaction mixture was heated to 90° C. for 12 h. Work up (EtOAc and H2O) followed by purification on combiflash using a gradient mixture of EtOAc and Petether (55:45) as eluent afforded the titled compound (3 mg) as an Off-White solid. MS (m/z): 439.5 [M+H]+.

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