Ethanesulfonamide → HCID 49819974, compound

Participants

Reaction Conditions

Reaction Steps

Titanium(IV) isopropoxide (234 μL, 0.800 mmol) was added dropwise to a mixture of 2-ethoxy-4-(5-formylpyridin-3-yl)benzonitrile (101 mg, 0.400 mmol), ethanesulfonamide (52.4 mg, 0.480 mmol) in toluene (20 mL). The resulting mixture was heated at 140° C. for 2 hr. After concentration, the residue was dissolved in CH2Cl2 (10 mL) and sodium triacetoxyborohydride (254 mg, 1.200 mmol) was added at room temperature. The resulting mixture was stirred overnight, and quenched with NaHCO3 solution. After filtration, extraction and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-3.5%) and yielded a colorless oil (100 mg) which turned to colorless solid after standing. ESI-MS m/z: 317.9 [M+H]+, 1H NMR (400 MHz, CDCl3): δ 1.40 (t, J=7.4 Hz, 3H), 1.53 (t, J=7 Hz, 3H), 3.08 (q, J=7.4 Hz, 2H), 4.25 (q, J=7 Hz, 2H), 4.43 (d, J=6.2 Hz, 2H), 4.59 (brs, 1H), 7.10 (d, J=1.4 Hz, 1H), 7.19 (dd, J=8, 1.6 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.93 (s, 1H), 8.62 (s, 1H), 8.77 (s, 1H).

Provenance & Evidence