[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2I)[CH:7]=1.C([Mg]Cl)(C)C.[CH2:17]([Sn:21]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])Cl)[CH2:18][CH2:19][CH3:20]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[Sn:21]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=1To a −16° C. solution of 6-fluoro-1-iodoimidazo[1,5-a]pyridine (158 mg, 603 μmol) in THF (4.64 mL) was added isopropylmagnesium chloride (368 μL, 736 μmol) dropwise. After 20 min tributylchlorostannane (232 mg, 193 μL, 712 μmol) was added dropwise at −16° C. and allowed to warm to room temperature. After 2 h the reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The phases were separated and the organic phase washed with brine. The organic layer was collected, concentrated in vacuo, and used in the next step without further purification.
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