4-Fluoro-N-methylaniline → [2-(4-fluoro-N-methylanilino)-4-pyridinyl]methanol

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CNc1ccc(F)cc1.OCc1ccnc(Cl)c1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>CN(c1ccc(F)cc1)c1cc(CO)ccn1

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온도: 105 °C

실험 절차

In a 50 mL round-bottomed flask (t=g) was (2-chloropyridin-4-yl)methanol (.1 g, 0.70 mmol), Pd2dba3 (0.032 g, 0.03 mmol), and biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol) in toluene (6 mL) to give a dark red solution. 4-fluoro-N-methylaniline (0.096 g, 0.77 mmol) and KOtBu (.323 g, 2.88 mmol) were added. Mixture was degassed by bubbling N2 for 20 minutes, then placed in oil bath at 105 °C. Reaction went for 3 hours, at which point LC/MS was taken. No product was observed.