Potassium Carbonate → HCID 86698754, compound

A mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (100 mg, 0.38 mmol) and N,N-dimethylformiminium chloride (97 mg, 0.76 mmol) in DMF (3 mL) and dioxane (0.6 mL) was stirred at room temperature for 30 min. Potassium carbonate (2 mL, 4 mmol, 2 N) was added to the mixture. Then 2-(4-bromo-2-fluorophenoxy)ethanol (89 mg, 0.38 mmol) and Pd(dppf)Cl2 (20 mg, 0.03 mmol) was added to the reaction. The mixture was degassed by passing nitrogen through the solution for 5 min. and stirred at 80° C. for 2 hrs. The reaction was cooled and concentrated. The residue was dissolved with EtOAc (100 mL), washed with water (30 mL), saturated ammonium chloride (30 mL), brine (30 mL), dried over sodium sulfate and concentrated to afford a crude product. The crude was further purified by silica gel chromatography (PE/EtOAc=20% to 50%) to give the title compound (40 mg, 30% yield) as a light yellow oil. 1H NMR (400 MHz, CD3OD) δ 9.89 (s, 1H), 8.17 (s, 1H), 8.11 (s, 1H), 7.62 (s, 1H), 7.20 (m, 3H), 4.18 (t, 2H), 3.93 (t, 2H).

1. customThe mixture was degassed
2. customfor 5 min.
3. stirringstirred at 80° C. for 2 hrs
4. temperatureThe reaction was cooled
5. concentrationconcentrated
6. dissolutionThe residue was dissolved with EtOAc (100 mL)
7. washwashed with water (30 mL), saturated ammonium chloride (30 mL), brine (30 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customto afford a crude product
11. customThe crude was further purified by silica gel chromatography (PE/EtOAc=20% to 50%)

ORD record

ord-66d2ce3946b549dfab8378ab5fb056a0

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2