1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 9-cyclopentyl-N-(6-(4-(dimethylamino)-1-piperidinyl)-3-pyridinyl)-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Steps

To a microwave reaction vessel were placed compound 4 (30 mg, 118 mmol), compound 91 (50 mg, 178 mmol), tris(dibenzylideneacetone)dipalladium(0) (5.4 mg, 5.9 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (8.6 mg, 15 mmol), and sodium tert-butoxide (34 mg, 355 mmol). 1,4-dioxane (4 mL) was added and the vessel was purged with N2 for 3 min, then capped and subjected to microwave irradiation for 2 h at 120° C. After removal of the volatiles, the residue was dissolved in methanol and filtered. The filtrate was subjected to reverse phase preparative HPLC (acetonitrile/water containing 0.1% TFA each, 40 min from 5 to 40%) to give ˜15 mg of compound 90 as a TFA salt. 1H NMR (400 MHz, CD3OD) δ 9.43 (1 H, s), 9.16 (1 H, s), 8.65 (1 H, d, J=2.3 Hz), 8.48-8.57 (2 H, m), 8.12 (1 H, dd, J=9.4, 2.3 Hz), 7.21 (1 H, d, J=9.4 Hz), 5.29-5.47 (1 H, m), 4.45 (2 H, d, J=13.7 Hz), 3.49-3.58 (1 H, m), 3.03-3.18 (2 H, m), 2.92 (6 H, s), 2.37-2.54 (2 H, m), 2.04-2.29 (6 H, m), 1.76-1.93 (4 H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 457.3, Calculated 457.2.

Provenance & Evidence