Trimethylsilyldiazomethane → HCID 178505452, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of TMS diazomethane (2 M in hexanes, 0.205 mL, 0.410 mmol) in anhydrous THF (1 mL) was added n-butyl lithium (2.5 M in hexanes, 0.164 mL, 0.410 mmol) dropwise@−5° C. The mixture was stirred to 20 min@−5° C. when this solution was added dropwise to a mixture of 6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (4-1, 0.050 g, 0.103 mmol) in THF (1 mL)@−5° C. The reaction was allowed to stir@−5° C. for 3 hr when it was quenched with saturated aqueous Na2HCO3 and extracted with CH2Cl2 (3×15 mL). The combined organics were dried (anhydrous Na2SO4), filtered, and concentrated. The residue was taken up in THF (2 mL) and TBAF (1 M in THF, 0.205 mL) was added. The reaction was heated to 60° C. for 2 hr, at which time it was cooled and concentrated. The resulting residue was taken up in DMF and purified by reverse phase HPLC (8-1; 5% CH3CN: 95% H2O+0.01% TFA to 95% CH3CN: 5% H2O+0.01% TFA). 1H-NMR (500 MHz, d6 DMSO) δ 9.74 (bs, 1H), 9.20 (d, J=2.20, 1H), 8.65 (bs, 1H), 8.29 (d, J=2.21, 1H), 7.60-7.70 (m, 1H), 7.25-7.55 (m, 12H), 7.18 (t, J=7.08, 1H), 4.35 (s, 2H), 3.50 (d, J=12.06, 2H), 3.25-3.39 (m, 1H), 3.09-3.20 (m, 2H), 2.29-2.39 (m, 2H), 1.97-2.10 (m, 2H). HRMS m/z (M+H) Calcd: 530.2463, found: 530.2454.

Provenance & Evidence