Phosphorus trichloride → HCID 135497089, compound

Participants

Reaction Steps

To a suspension of 1-[(6-chloro-1-oxidopyridin-3-yl)methyl]-4-methylpiperazine (0.145 g, 0.60 mmol) and 2-oxoindoline-6-carbonitrile (0.100 g, 0.63 mmol) in tetrahydrofuran (3 mL), was added sodium bis(trimethylsilyl)amide (1.4 mL, 1.4 mmol). The mixture was stirred for 5 min at room temperature and then heated in a microwave oven at 110° C. for 10 min. The mixture was quenched with methanol (2 mL) followed by evaporation to dryness. The dry product mixture was dissolved in ethyl acetate/acetonitrile, (1:1, 5 mL), is and phosphorus trichloride (0.5 mL, 5.73 mmol) was added. The mixture was stirred at 60° C. for 3 h and then concentrated in vacuo. The residue was purified on a silica gel column using a gradient dichloromethane/methanol, (100:1 to 2:1), as the eluent. The resulting yellow solid was dissolved in dichloromethane/methanol, (9:1), and treated with HCl in diethyl ether (1 M) at 0° C. The resulting yellow crystals were collected by filtration and washed with diethyl ether to obtain 0.025 g (9% yield) of the title compound: MS (ESP) m/z 348 (M++1).

Provenance & Evidence