Potassium Phosphate, Tribasic → HCID 68328328, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added N-isopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (167 mg, 0.379 mmol), 2-chloro-6-cyclopropylpyrazine (CombiPhos Catalyst Inc., 64.5 mg, 0.42 mmoles), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (10.9 mg, 0.023 mmol), Pd2(dba)3 (10.4 mg, 0.011 mmol), and K3PO4 (242 mg, 1.138 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and H2O (0.4 mL) and heated in the microwave at 120° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification with flash chromatography (eluting with 5-100% EtOAc in Hex) afforded 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (104.4 mg, 54%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 515.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.87 (1H, s), 8.74 (1H, s), 8.42 (1H, s), 8.16 (1H, s), 8.07-8.11 (1H, m), 7.98-8.03 (1H, m), 7.84 (2H, d, J=8.4 Hz), 7.28 (2H, s), 3.97-4.08 (1H, m), 2.36 (3H, s), 2.14 (1H, td, J=8.5, 4.2 Hz), 1.35 (6H, d, J=6.5 Hz), 1.24-1.30 (2H, m), 1.10-1.17 (2H, m).

Provenance & Evidence