Phenylboronic Acid → HCID 59593176, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 from Example 12 (0.2 g, 0.6 mmol), phenylboronic acid (70 mg, 0.6 mmol), and bis(triphenylphosphine)palladium(II) dichloride (20 mg, 30 μmol) in 1 M aqueous Na2CO3 (1 mL) and acetonitrile (1 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (210 mg, 0.87 mmol) and bis(triphenylphosphine)palladium(II) dichloride (20 mg, 30 μmol) were added and the mixture was heated to 150° C. in a sealed microwave reactor for 20 min. The mixture was extracted with EtOAc and CH2Cl2. The combined organics were concentrated to yield 419 after reverse phase HPLC purification (45 mg). MS (Q1) 414 (M)+

Provenance & Evidence