Water → (4-Chlorophenyl)-[4-(hydroxypyridin-4-yl-methyl)-1-methyl-1H-pyrrol-2-yl]-methanone

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Reaction Steps

A solution of 1.36 g (8.64 mmol) of 4-bromopyridine in 12 mL of ether was cooled to −40° C. under argon and 5.4 mL (8.64 mmol) of 1.6 M n-butyllithium in hexane was added dropwise. A solution of 1.07 g (4.3 mmol) of 5-(4-chloro-benzoyl)-1-methyl-1H-pyrrole-3-carboxaldehyde (obtained from Procedure 5) in 15 mL of THF was added dropwise (exotherm). The reaction was stirred for 5 min and poured into water and extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The residue was flash chromatographed (50%acetone/hexane). The trailing spot was concentrated and recrystallized from EtOAc to give 0.74 g (52% yield) of the title compound as a white solid: mp 145-146° C. ES-MS m/z=327 (M++H). 1H NMR (300 MHz, CDCl3) δ 2.55 (s, 1H); 4.0 (s, 3H); 5.8 (s, 1H); 6.56 (s, 1H); 6.8 (s, 1H); 7.3 (dd, 2H); 7.4 (dd, 2H); 7.75 (dd, 2H); 8.55 (dd, 2H). Anal calc'd for C18H15ClN2O2: 66.16; H, 4.63; N, 8.57. Found: C, 65.8; H, 4.65; N, 8.63.

Provenance & Evidence