Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[N:15]1([C:2]2[CH:3]=[CH:4][C:5]3[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=3[CH:14]=2)[CH:19]=[CH:18][CH:17]=[N:16]1
2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.54 g, 2.1 mmol), pyrazole (0.29 g, 4.3 mmol), copper(I) iodide (0.062 g, 0.33 mmol) and potassium carbonate (0.30 g, 2.2 mmol) were stirred in dry DMF (3 mL) under nitrogen and heated at 150° C. for 18 h. The reaction mixture was cooled and extracted from water into dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was used in the next step without further purification.
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