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Substitution (Br)



Example 1

NaH (60%, 1.64 g, 41 mmol) was slowly added to a suspension of the SM (12 g, 27.4 mmol) in DMF (180 mL) at RT under N2. The mixture was stirred for 2 h. To the mixture was then added the alkyl bromide (7 mL, 32.8 mmol). The reaction mixture was stirred for 15 h. The mixture was poured into an aq solution of K2CO3 and extracted with EtOAc. The org layer was concentrated to dryness. The crude material was taken up in DCM, dried (MgSO4), and concentrated to dryness. The resulting material was purified by Prep LC (330 g silica, 100% DCM to 95% DCM/5% MeOH/0.1% NH4OH) to provide the product. [15.52 g, 95%]

[Patent Reference: WO2015144799, page 93, (18.8 MB)]