1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 59186503, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine (50.0 mg, 0.299 mmol, 1.2 equiv), 2-iodo-5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine (0.100 g, 0.249 mmol, 1 equiv), tris(dibenzylideneacetone)dipalladium (0) (17.0 mg, 0.019 mmol, 0.075 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (21.6 mg, 0.037 mmol, 0.150 equiv), and sodium tert-butoxide in dioxane (2 mL) was heated at 160° C. for 15 min under microwave radiation. The reaction mixture was partitioned between half saturated aqueous sodium chloride solution and ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative HPLC provided product (11.5 mg, 11% yield). 1H NMR (400 MHz, DMSO-d6), δ: 9.28 (s, 1H), 8.79 (s, 1H), 8.35 (d, J=7.9 Hz, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.87 (dd, J=16.6, 8.8 Hz, 2H), 7.66 (dd, J=8.7, 7.3 Hz, 1H), 7.55 (m, 1H), 7.40 (m, 1H), 7.21 (m, 1H), 4.31 (m, 1H), 3.95 (d, J=11.1 Hz, 2H), 3.52-3.39 (m, 2H), 2.07 (s, 3H), 1.89 (m, 4H).

Provenance & Evidence