3-Bromoquinoline → HCID 18187735, compound

Participants

Reaction Steps

A solution of 260 mg (1.15 mmol) of 1-(t-butoxycarbonyl)-4-(prop-2-enyl)piperidine (from EXAMPLE 33, Step B) in 3 mL of THF under argon was treated with 2.30 mL of 0.5 M 9-BBN solution in THF. The resulting mixture was stirred at rt for 2 h, then treated with 68 mg (1.25 mmol) of NaOMe. The resulting mixture was stirred until it was homogeneous (˜15 min) and then was treated with 0.155 mL (1.15 mmol) of 3-(bromo)quinoline and 41 mg (0.05 mmol) of [1,1′-bis(triphenyl-phosphino)ferrocene]dichloropalladium.CH2Cl2. The resulting mixture was heated at reflux for 30 min, cooled and quenched with 20 mL of 1.0 N NaOH. The quenched reaction was extracted with 2×50 mL of ether; the extracts were dried over MgSO4, combined and concentrated. Flash chromatography on 15 g of silica gel using 4:1 v/v hexanes/EtOAc as the eluant afforded 240 mg (59%) of the title compound: 1H NMR (300 MHz) B 1.00-1.16 (m, 2H), 1.25-1.40 (m, 2H), 1.45 (s, 9H), 1.60-1.80 (5H), 2.62-2.72 (m, 2H), 2.79 (t, J=7.8,22H), 4.06 (br s, 2H), 7.52 (m, 1H), 7.66 (m, 1H), 7.76 (dd, J=8.0, 1.6, 1H), 7.91 (d, J=1.6, 1H), 8.77 (d, J=2.2, 1H).

Provenance & Evidence