Sodium Carbonate → 5-(3-Benzyloxy-1-fluoro-7-vinylnaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Participants

Reaction Conditions

Reaction Steps

To a microwave vial is added 5-(3-benzyloxy-7-bromo-1-fluoronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (340 mg, 0.73 mmol) (intermediate from preparing Example 16), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.24 mL, 1.46 mmol), polystyrene tetrakis(triphenylphosphine)palladium(0) (0.1 mmole/g) (365 mg, 0.0365 mmol), Na2CO3 (2 M, 1.83 mL, 3.65 mmol) and DME (2.5 mL). The mixture is then heated in a microwave at 110° C. for 30 min. The resin is then filtered and the residue is purified quickly by Biotage reverse phase, eluting with 10-90% EtOH/water to give fractions containing the title compound: MS (M+H)+=413. The fractions are combined and used in the next step without concentration.

Provenance & Evidence