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14th December 2017 @ 15:03

VTM012.jpg

VTM012                                                                                                      17/11/2017

VTM010 (0.05 g, 0.12 mmol) was dissolved in degassed toluene (2 mL). Piperidine (0.025 g, 0.29 mmol), NaOtBu (0.016 g, 0.168 mmol), JohnPhos (1.6 mg, 5.4 μmol) and Pd 2 (dba) 2 (0.3 mg, 0.6 μmol) were added to the solution and stirred at 100°C for two weeks. The reaction was quenched with 2M HCl and the organic layer extracted (EtOAc 3x2 mL). The crude was concentrated under reduced pressure and purified via column chromatography (100% EtOAc).

VTM012 COLUMN.jpeg
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14th December 2017 @ 10:41

VTM011.jpg

VTM011                                                                                                    17/11/2017

 

VTM010 (0.05 g, 0.12 mmol) was dissolved in degassed toluene (2 mL). Pyrrolidine (0.02 g, 0.288 mmol), NaO t Bu (0.016 g, 0.168 mmol), JohnPhos (1.6 mg, 5.4 μmol) and Pd 2 (dba) 2 (0.3 mg, 0.6 μmol) were mixed in this order and stirred for two weeks at 100°C. The reaction was quenched (2M HCl). The organic layer was extracted (3x2mL EtOAc). The crude was concentrated in vacuo and purified via column chromatography (EtOAc).

VTM011COLUMN.jpg

NMR analysis suggested that a final product was not formed.

Attached Files
14th December 2017 @ 10:07

VTM010.jpg

 VTM010                                                                                                    07/11/2017

VTM009 (0.738 g, 1.22 mmol) was added to a solution of 3,4-difluorophenyl-1-ol (0.60 g, 4.16 mmol) in dry THF (30 mL). The mixture was cooled down to 0°C and NaH (60%, 0.17 g, 6.93 mmol)was added. The mixture was stirred at room temperature for 2 hours. The reaction was quenched with HCl (30mL) and the organic layer extracted with EtOAc (3x30 mL) and 2M HCl (3x10 mL). The crude was concentrated under reduced pressure

VTM010 CRUDE (2).jpg

and purified via column chromatography (100% EtOAc) to yield the final product (0.50 g, 48%) as a beige solid.

VTM010 PRODUCT (3).jpg
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