Lithium diisopropylamide → HCID 69434605, compound

Participants

Reaction Conditions

Reaction Steps

4-(5-Chloro-2-methoxy-phenyl)-3-(3-hydroxy-propenylsulfanyl)-6-trifluoromethyl-4a,8a-dihydro-1H-quinolin-2-one (Ig) was prepared by a base-mediated epoxide rearrangement process. To a solution of VIII (0.2 g, 0.45 mmol) in dry THF (4 mL) at −78° C. under nitrogen was added a THF solution of lithium diisopropylamide (LDA, used as supplied by Aldrich, 1.5 Molar, 0.6 mL). The mixture was stirred at −78° C. for a further 10 min. before it was allowed to warm to room temperature and stirring was continued for another 30 min. It was quenched with saturated solution of NH4Cl, organic residues were extracted into ethyl acetate. The organic layers were combined and dried over MgSO4. Evaporation of solvent gave 0.18 g (90% yield) of the desired product as pale yellow solid, mp 148–150° C. Calcd. for C20H15Cl1F3N1O3S1: C, 54.34; H, 3.42; N, 3.17; F, 12.90; Cl, 8.02. Found: C, 54.34; H, 3.66, N, 2.93; F, 12.80; Cl, 7.95. 1H NMR (300 MHz, DMSO-d6) δ 12.51 (s, 1H), 7.84 (d, J=10.2 Hz, 1H), 7.58–7.54 (m, 2H), 7.30–7.23 (m, 2H), 7.08 (s, 1H), 6.28 (d, J=15.3 Hz, 1H), 5.58 (dt, J=15.3, 5.4 Hz, 1H), 4.74 (t, J=5.7 Hz, 1H), 3.84 (t, J=6.0 Hz, 2H), 3.69 (s, 3H).

Provenance & Evidence