Potassium Phosphate, Tribasic → HCID 86698779, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-tert-butyl 3-methyl 5-bromo-6-chloro-1H-indole-1,3-dicarboxylate (300 mg, 0.78 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (255 mg, 1.16 mmol), 1,4-dioxane (4.2 mL) and aqueous potassium phosphate tribasic (4.6 mL, 0.5M, 2.3 mmol) was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (57 mg, 0.78 mmol). The pink mixture was evacuated and refilled with nitrogen three times. The sealed reaction was heated at 85° C. for 10 minutes. The cooled reaction mixture was filtered through Celite, and the filter pad was washed with water followed by three washes with ethyl acetate. The filtrate layers were separated, and the aqueous layer was extracted again with ethyl acetate. The organic extracts were combined, washed with brine and then dried over sodium sulfate. The mixture was filtered and concentrated in vacuo to give an oily solid which was purified by flash chromatography eluting with heptanes/ethyl acetate (90:10 to 40:60) to give the title compound (279 mg, 89% yield) as a white solid. MS (ES+) 302 (M-Boc+1)+. 1H NMR (500 MHz, DMSO-d6) δ 9.62 (s, 1H), 8.26 (s, 1H), 8.21 (s, 1H), 7.95 (s, 1H), 7.26 (d, J=8.29 Hz, 2H), 6.86 (d, J=8.54 Hz, 2H), 3.32 (s, 3H), 1.66 (s, 9H).

Provenance & Evidence