Water → HCID 57585828, compound

Participants

Reaction Conditions

Reaction Steps

A flask charged with 1,1-dimethylethyl (5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate (3.0 g, 9.26 mmol; step 1 above), dppf (645 mg, 1.16 mmol), Pd2dba3 (532 mg, 0.58 mmol), ZnCN2 (1.50 g, 12.8 mmol) and water in 50 mL DMF was evacuated/backfilled with nitrogen (×4), and stirred at 110° C. for 21 hours. Upon cooling, the mixture was diluted with satd NH4Cl and extracted with ethyl acetate. The organic extract was washed with (water 3×, brine), dried over MgSO4 and concentrated in vacuo. The residual oil was purified by flash chromatography (ethyl acetate/hexanes) affording title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1 H), 7.45 (d, 1 H, J=7.9 Hz), 7.28 (d, 1 H, J=7.7 Hz), 4.69 (br.s, 1 H), 4.47 (br. s, 1 H), 3.33-3.25 (m, 2H), 2.86-2.80 (m, 2H), 2.79 (s, 9H).

Provenance & Evidence