Potassium Carbonate → HCID 57386412, compound

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (Isomeric mixture 1 from Example 49 Step 4, 0.08 g, 0.20 mmol), 3-chlorophenylboronic acid (0.046 g, 0.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.015 g, 0.02 mmol), 2 M aq. K2CO3 solution (0.197 mL, 0.39 mmol) and 1,4-dioxane (1.5 mL) were mixed in a vial and heated in a microwave reactor at 130° C. for 20 min. When cooled to r.t. the mixture was diluted with DCM, washed with water and dried over Na2SO4. The filtrate was concentrated and the product purified by preparative chromatography to yield Isomeric mixture 1 of the title compound (30 mg, 35% yield): 1H NMR (500 MHz, CDCl3) δ ppm 1.28 (m, 7 H), 1.48 (m, 3 H), 1.64 (d, 1 H), 1.91 (t, 1 H), 2.11 (m, 1 H), 2.40 (s, 3 H), 2.51 (t, 1 H), 3.74 (td, 1 H), 3.85 (td, 1 H), 4.48 (dd, 1 H), 6.81 (d, 1 H), 7.01 (d, 1 H), 7.26 (m, 1 H), 7.32 (d, 2 H), 7.40 (m, 2 H); MS (ES+) m/z 438 [M+H]1.

Provenance & Evidence