Tetrahydrofuran → 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-4-benzimidazoyl-2-propanol

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Reaction Steps

To methyl 1-(2,6-difluorobenyl)-2-(2,6-difluorophenyl)benzimidazole-4-carboxylate (Example 102) (1.02 g, 2.46 mmol) suspended in THF (5 mL) was added 1.4 M methyl lithium (0.95 mL). After 0.5 h, the reaction was diluted with EtOAc and washed with NaHSO4 (10% soln) and NaCl(sat. aq). The combined washings were dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with 1:1 ethylacetate/hexane and recrystallization from hexane, yielding white crystals of 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-4-benzimidazoyl-2-propanol (0.11 g, 0.27 mmol, 55% yield). M.p. 149-150° C. 1H-NMR (200 MHz, CD2Cl2): δ7.55 (m, 1H, H4′), 7.48 (d, J=8.1 Hz, 1H, H5), 7.25 (m, 2H, H6,4″), 7.16 (dd, J=1.1, 7.6 Hz, 1H, H7), 7.10 (m, 2H, H3′,5′), 6.82 (m, 2H, H3″,5″), 5.82 (s, 1H, OH), 5.37 (s, 2H, CH2PhF2), 1.67 (s, 6H, CH3). Anal. (C23H18F4N2O) C,H,N.

Provenance & Evidence