2-Bromothiazole → HCID 58438508, compound

Participants

Reaction Steps

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-one (SM-1a, 350 mg, 0.95 mmol) and 2-bromothiazole (156 mg, 0.95 mmol) were combined in DME (10 mL), and the mixture was purged with nitrogen for 10 minutes. Aqueous sodium carbonate solution (2M, 0.95 mL) and Pd(dppf)Cl2 (34 mg, 5 mol %) were added. The solution was purged with nitrogen for 10 minutes and was heated at reflux for 5 hours. The reaction was cooled and held at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water and separated. The aqueous layer was washed with 15 mL ethyl acetate (2×), and the combined organic portions were washed with brine and dried over MgSO4. Filtration and solvent removal afforded the crude product as a brown paste which was purified by silica chromatography on Combiflash ISCO purification system (Teledyne Corp., Lincoln Nebr.) eluting with a heptanes/ethyl acetate gradient. The final product was obtained as a light yellow flaky solid (SM-1f, 195 mg, 95%). MS (ES+) 216.2, 1H NMR (CDCl3) δ 2.72-2.75 (m, 2H), 3.20 (t, 2H), 7.42 (d, 1H), 7.80 (d, 1H), 7.92 (d, 1H), 7.94-7.97 (m, 1H), 8.10 (br s, 1H).

Provenance & Evidence