4-Methoxypyridine-3-boronic acid → HCID 59593086, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.1 g, 0.3 mmol), 4-Methoxy-3-pyridineboronic acid (42 mg, 0.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 μmmol) in 1 M aqueous Na2CO3 (0.5 mL) and acetonitrile (0.5 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (122 mg, 0.5 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 mop, 1 M aqueous Na2CO3 (1 mL), and acetonitrile (1 mL) were added into the same pot. The reaction 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 361 after reverse phase HPLC purification (28 mg). MS (Q1) 459 (M)+

Provenance & Evidence