[N:1]1([C:6]2[CH:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][N:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.P(Br)(Br)[Br:15].C1COCC1.C([O-])(O)=O.[Na+]>C(OCC)C.C(OCC)(=O)C>[Br:15][CH2:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:11]=1
To a stirred solution of (2-(1H-pyrazol-1-yl)pyridin-4-yl)methanol (175 mg, 1.00 mmol) in diethyl ether (5 mL), PBr3 (0.11 mL, 1.00 mmol) was added dropwise at 0° C. Then THF (5 mL) was added to the resulting white precipitate and the mixture was heated at 65° C. for 1 h. The mixture was cooled to rt, diluted with ethyl acetate (5 mL) and poured into saturated aqueous NaHCO3 solution (5 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield the title compound (165 mg, 70%). [LCMS RtE=1.33 min, [M+H]+=237.9/239.9].
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