Potassium Carbonate → HCID 57813523, compound

Participants

Reaction Conditions

Reaction Steps

Pd(OAc)2 (25.8 mg, 0.115 mmol), PPh3 (120.6 mg, 0.46 mmol), K2CO3 (794.0 mg, 5.75 mmol) and 1,1-dimethylethyl [(3-bromo-2-methylphenyl)methyl]carbamate (1.15 g, 3.85 mmol) were suspended in anhydrous 1,4-dioxane (20 mL) under nitrogen. After the mixture was heated to 60° C. for 30 min, [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (2.04 g, 4.62 mmol) was added. Then the mixture was stirred overnight at 100° C. After cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (20 mL), and then the solution was washed with water (7 mL), brine (7 mL), and, dried over anhydrous Na2SO4. After silica column chromatography, eluted with PE:EA=30:1, 1.1 g of the product was obtained, as a colorless liquid. (Yield: 65%). 1H NMR (400 MHz, CDCl3): 0.10 (s, 6 H), 0.94 (s, 9 H), 1.47 (s, 9 H), 2.19 (s, 3 H), 4.38 (d, J=5.2 Hz, 2 H), 4.76 (br, 1 H), 4.78 (s, 2 H), 7.14-7.39 (m, 7 H). 13C NMR (100 MHz, CDCl3): δ −5.2, 16.1, 18.4, 25.9, 28.4, 43.4, 64.9, 79.4, 124.6, 125.6, 127.0, 127.9, 129.3, 133.7, 136.9, 141.2, 141.9, 143.0, 155.7; HPLC: retention time: 4.987 min; purity: 98.9% (HPLC).

Provenance & Evidence