HCID 86674839, compound → HCID 53236853, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methylmagnesium bromide (519 μl, 1.558 mmol) was added dropwise to a solution of 2-chloro-4-(4-formylpyridin-3-yl)benzonitrile (126 mg, 0.519 mmol) in dry THF (15 mL) at −50° C. The resulting mixture was slowly warmed up to 0° C. during 2 hr. The reaction was quenched by NH4Cl (solution). After extraction with CH2Cl2, dry over Na2SO4, filtration, concentration again, the residue was purified by column (CH2Cl2-MeOH, v/v, 1-3.5%) and yielded 120 mg of 2-chloro-4-(4-(1-hydroxyethyl)pyridin-3-yl)benzonitrile. ESI-MS m/z: 259 [M+1]+, Retention time 1.11 min; 1H-NMR (MeOD, 400 MHz) δ 1.29 (d, J=6.4 Hz, 3H), 4.83 (q, J=6.4 Hz, 1H), 7.50 (dd, J=8.0, 1.6 Hz, 1H), 7.71 (d, J=1.6 Hz, 1H), 7.73 (d, J=5.6 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 8.35 (s, 1H), 8.61 (d, J=5.6 Hz, 1H).

Provenance & Evidence