Hexane → HCID 59807120, compound

Participants

Reaction Steps

A suspension of tris(dibenzylideneacetone)dipalladium(0) (66 mg, 0.072 mmol) in anhydrous THF (3 mL) was treated with tri-t-butylphosphine in hexane (10% wt) (0.435 mL, 0.143 mmol) and the mixture stirred for 5 minutes at room temperature. A solution of tert-butyl 2-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethyl(ethyl)carbamate (compound 5, 0.275 g, 0.717 mmol) in THF (7 mL) was added followed by Lithium bis(trimethylsilyl)amide (1M in THF, 1.435 mL, 1.435 mmol) and the mixture heated in a sealed reaction vial at 90° C. for 3 hours. The mixture was cooled to room temperature and treated with TBAF (1M in THF, 4 mL, 4 mmol) for 30 minutes. The mixture was partitioned between water (10 mL) and ethyl acetate (100 mL), transferred to a separatory funnel and the organic layer separated. The aqueous layer (pH=10) was further extracted with ethyl acetate and the combined organic layers washed with brine, dried over Na2SO4, filtered and concentrated to give a dark brown residue. Purification on silica gel eluting with 2.5% 2M NH3 in methanol/97.5% dichloromethane yielded a brown residue, 6 (171 mg, 74.6%). 1H-NMR ((DMSO-d6) δ 6.42 (d, 1H, J=8.5 Hz), 6.31-6.26 (m, 1H), 6.22 (br s, 1H), 4.20 (br s, 2H), 3.26-3.08 (m, 8H), 2.55 (t, 2H, J=6.3 Hz), 1.82-1.74 (m, 2H), 1.41 (s, 9H), 1.02 (t, 3H, J=7.0 Hz). MS (ESI+): 320 (MH+, 90), 264 (100).

Provenance & Evidence