Dichloromethane → HCID 69938143, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of 4-cyano phenylboronic acid (220 mg, 1.50 mmol), 1-(3-Bromo-pyridin-4-yl)-ethanol (303 mg, 1.50 mmol) and PdCl2(dppf). CH2Cl2 adduct (98 mg, 0.12 mmol) in DMF (6 mL) was added 2M Na2CO3 solution (1.50 ml, 3.00 mmol) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and sat. NH4Cl solution. After extraction with DCM and separation, the combined extracts were concentrated and purified by ISCO 12 g (10% MeOH/DCM=0-25%) to give 4-[4-(1-Hydroxy-ethyl)-pyridin-3-yl]-benzonitrile (18, 170 mg, 51%) as a white solid; ESI-MS m/z 225 [M+H]+, Retention time 0.97 min. 1H-NMR (MeOD, 400 MHz) δ 1.28 (d, J=6.4 Hz, 3H), 4.85 (q, J=6.4 Hz, 1H), 7.56 (d, J=8.4 Hz, 2H), 7.73 (d, J=5.2 Hz, 1H), 7.86 (d, J=8.4 Hz, 2H), 8.33 (s, 1H), 8.59 (d, J=5.2 Hz, 1H)

Provenance & Evidence