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17th October 2017 @ 10:13

VTM003                                                                                                                                                                 10/10/2017

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VTM002 (1.49g, 4.78mmol) was dissolved in DCM (40mL). BAIB (1.644g, 5.10mmol) was cautiously added to the solution and the reaction was stirred over 5 days at room temperature. The reaction was quenched with aqueous saturated NaHCO3 (30mL) and the organic layer extracted ( CH2Cl2 3 x 30mL; brine 3x20mL). The crude was concentrated under reduced pressure to give a light brown powder.

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The crude reaction mixture was purified via column chromatography (40% to 70% EtOAc in Petroleum Ether) to afford the product (0.40g, 27%) as a brown solid.

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Attached Files
17th October 2017 @ 09:43

VTM002                                                                                                                       09/10/2017

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4-bromobenzaldehyde (2.02 g, 10.9 mmol) was added to a solution of 2-chloro-6-hydrazineylpyrazine (1.60 g, 11.1 mmol) in EtOH (35 mL) and stirred at room temperature for 16 hours. TLC

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suggested reaction completion. The mixture was filtered and washed with EtOH (10 mL). The light beige solid was collected (2.23 g, 66 %)

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Attached Files
10th October 2017 @ 12:27

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3,4-difluorophenyl acetic acid was mixed with 1M LiAlH 4 in THF (6.3 mL, 6.3 mmol) at 0°C and stirred for 24 hours. It was then heated to reflux for an hour and cooled down to room temperature. The mixture was treated with 2M HCl (40 mL) and EtOAc (40mL). The organic layer was extracted (2 x 20mL EtOAc) and concentrated in vacuo. The crude was obtained as a pale yellow oil and purified via column chromatography (Petroleum Ether 1:1 EtOAc) to yield clear liquid as a final product (0.3 g, 33 %)

Attached Files