diethyl (E)-pent-2-enedioate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 15 mL (85.6 mmol) of diethyl (2E)-pent-2-enedioate in 5 mL of anhydrous DMF are added, under a stream of argon, 0.62 g (2.8 mmol) of Pd(OAc)2, 1.7 g (5.56 mmol) of P(OTol)3 and 5.5 mL (39.7 mmol) of Et3N, the medium is then heated to 40° C. and 4 mL (39.75 mmol) of 3-bromopyridine are added. The medium is then heated for 24 hours at 90° C., and then taken up in 100 mL of EtOAc, washed with 100 mL of water, dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 9.12 g of diethyl (2Z)-3-(pyridin-3-yl)pent-2-enedioate are obtained in the form of a yellow wax. The medium is then heated for 24 hours at 90° C. washed with 100 mL of water dried over Na2SO4 concentrated under reduced pressure purified by chromatography on a column of silica gel eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 15 mL (85.6 mmol) of diethyl (2E)-pent-2-enedioate in 5 mL of anhydrous DMF are added, under a stream of argon, 0.62 g (2.8 mmol) of Pd(OAc)2, 1.7 g (5.56 mmol) of P(OTol)3 and 5.5 mL (39.7 mmol) of Et3N, the medium is then heated to 40° C. and 4 mL (39.75 mmol) of 3-bromopyridine are added. The medium is then heated for 24 hours at 90° C., and then taken up in 100 mL of EtOAc, washed with 100 mL of water, dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 9.12 g of diethyl (2Z)-3-(pyridin-3-yl)pent-2-enedioate are obtained in the form of a yellow wax. The medium is then heated for 24 hours at 90° C. washed with 100 mL of water dried over Na2SO4 concentrated under reduced pressure purified by chromatography on a column of silica gel eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 15 mL (85.6 mmol) of diethyl (2E)-pent-2-enedioate in 5 mL of anhydrous DMF are added, under a stream of argon, 0.62 g (2.8 mmol) of Pd(OAc)2, 1.7 g (5.56 mmol) of P(OTol)3 and 5.5 mL (39.7 mmol) of Et3N, the medium is then heated to 40° C. and 4 mL (39.75 mmol) of 3-bromopyridine are added. The medium is then heated for 24 hours at 90° C., and then taken up in 100 mL of EtOAc, washed with 100 mL of water, dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 9.12 g of diethyl (2Z)-3-(pyridin-3-yl)pent-2-enedioate are obtained in the form of a yellow wax. The medium is then heated for 24 hours at 90° C. washed with 100 mL of water dried over Na2SO4 concentrated under reduced pressure purified by chromatography on a column of silica gel eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc