3-(Methylsulfonyl)phenylboronic acid → HCID 59593102, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.6 g, 1.5 mmol), 3-(methylsulfonyl)phenylboronic acid (0.3 g, 1.5 mmol), and bis(triphenylphosphine)palladium(II) dichloride (53 mg, 80 μmol) in 1 M aqueous Na2CO3 (3 mL) and acetonitrile (3 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion the organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organics were concentrated in vacuo. A portion of the residue (0.38 mmol) was dissolved in 1 M Na2CO3 (1.5 mL) and CH3CN (1.5 mL) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 (0.2 g, 0.8 mmol) and bis(triphenylphosphine)palladium(II) dichloride (13 mg, 20 μmol) were added into the same pot. The reaction mixture was heated to 150° C. in a sealed microwave reactor for 30 min. The mixture was extracted with EtOAc and CH2Cl2. The combined organics were concentrated to yield 360 after reverse phase HPLC purification (90 mg). MS (Q1) 506 (M)+

Provenance & Evidence