Tetrahydrofuran → HCID 59174872, compound

Participants

Reaction Conditions

Reaction Steps

A thick slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (2.50 g, 7.1 mmol) and bis(4-(di-tert-butylphosphino)-N,N-dimethyl-benzenamine) palladium dichloride (0.10 g, 0.14 mmol) in benzylzinc(II) bromide 0.5M in THF (21 mL, 11 mmol) was flushed with argon and sealed, and heated to 70° C. All solids eventually dissolved over 1 h to give a dark brown solution. After 3 h, the reaction mixture was cooled and diluted with sat'd aq. NH4Cl. Solid formed, and was taken up in EtOAc. The organic layer was washed sat'd aq. NH4Cl, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was suspended in 50 mL MTBE and stirred for 30 min, then filtered, rinsing with a minimum amount of MTBE, and dried in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine as a gray solid. MS (ESI) m/z: Calculated: 406.1; Observed: 407.1 (M++1).

Provenance & Evidence