Potassium Phosphate, Tribasic → N'-(3-chloro-6-fluoro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)-N-(1,4-dioxan-2-ylmethyl)-N-methylsulfamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-chloro-6-fluoro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl trifluoromethanesulfonate (200 mg, 0.49 mmol) in 1,4-dioxane (7 mL) were added N-(1,4-dioxan-2-ylmethyl)-N-methylsulfamide (200 mg, 0.98 mmol), Pd2(dba)3 (68 mg, 0.074 mmol), Xantphos (85 mg, 0.15 mmol), and K3PO4 (280 mg, 1.3 mmol). The reaction mixture was purged with N2 for 5 min, heated to 110° C. 8 h, cooled to room temperature, diluted with water, and extracted with CH2Cl2 (×3). The combined organics were dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.78 (d, 1H); 8.24 (d, 1H); 7.99 (d, 1H); 7.93 (t, 1H); 7.36 (d, 1H); 7.21 (br s, 2H); 3.64-4.00 (series of m, 7H); 3.36 (dd, 1H); 3.08 (dd, 1H); 2.99 (s, 3H). LRMS (ESI) calc'd for (C20H19ClFN3O5S) [M+H]+, 468.1; found 468.0.

Provenance & Evidence