Toluene → HCID 57576218, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diisobutyl aluminum hydride in toluene (1M, 652 μL, 0.652 mmol) was added to a stirred solution of a 3:1 mixture of ethyl 3-iodoquinoline-2-carboxylate and 3-methylbutyl 3-iodoquinoline-2-carboxylate (100 mg, 0.297 mmol) in dry THF (3 mL) at 0° C. under N2. The reaction was stirred for 4 h at 0° C. The reaction was quenched with saturated NH4Cl (5 mL) and water (5 mL) and extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. Sodium borohydride was added to a stirred solution of the crude product in EtOH (3 mL) and the reaction was stirred at room temperature for 20 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-50% EtOAc in hexanes gradient) to afford (3-iodoquinolin-2-yl)methanol, as a colorless solid. Rf=0.88 (50% EtOAc/hexanes). LCMS calc.=286.0; found=286.0 (M+1)+. 1H NMR (500 MHz, CDCl3): δ 8.56 (s, 1H); 8.03 (d, J=8.4 Hz, 1H); 7.74-7.71 (m, 1H); 7.70 (d, J=8.1 Hz, 1H); 7.54 (t, J=7.1 Hz, 1H); 4.90 (br s, 1H); 4.78 (s, 2H).

Provenance & Evidence