Sodium Carbonate → HCID 90412219, compound

Temperature

65 °C

A sealed tube was charged sequentially with 2-iodofuran (400 mg, 2.061 mmol), 1-chloro-4-ethynylbenzene (280 mg, 2.061 mmol), L-proline (47.4 mg, 0.412 mmol), Na2CO3 (44 mg, 0.412 mmol), sodium ascorbate (82 mg, 0.412 mmol), DMSO-H2O (9:1; 9 ml), NaN3 (160 mg, 2.47 mmol) and CuSO4.5H2O (514 mg, 2.061 mmol). The tube was sealed and stirred at 65° C. for 16 hours. The reaction mixture was then poured into a cold ammonium hydroxide solution, and the mixture was extracted with ethyl acetate (3×30 ml). The combined organic layers were washed with brine solution (30 ml), dried over sodium sulfate, and evaporated to yield the crude product, which was purified by column chromatography with 20% ethyl acetate/hexane to yield 4-(4-chlorophenyl)-1-(furan-2-yl)-1H-1,2,3-triazole (6 mg, 1.2%) as a pale yellow solid. The HPLC purity of the final product was 93.6%. LC-MS [M+1] 246 (C12H8ClN3O+H expected 246.04). The 1H-NMR spectra was in accordance with the chemical structure.

1. customThe tube was sealed
2. extractionthe mixture was extracted with ethyl acetate (3×30 ml)
3. washThe combined organic layers were washed with brine solution (30 ml)
4. dry with materialdried over sodium sulfate
5. customevaporated
6. customto yield the crude product, which
7. customwas purified by column chromatography with 20% ethyl acetate/hexane

ORD record

ord-fe64b0bceb7c45e4881e0c5c24cee561

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09402397B2