[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]2[CH:9]=[CH:10][S:11][C:3]=12.[CH3:12][C@@H:13]([OH:16])[C:14]#[CH:15].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[C:7]([C:15]#[C:14][C@H:13]([OH:16])[CH3:12])=[CH:6][N:5]=[C:4]2[CH:9]=[CH:10][S:11][C:3]=12
A mixture of 7-chloro-6-iodothieno[3,2-b]pyridine (0.46 g, 1.6 mmol), bis(triphenylphosphine)palladium(II) chloride (0.11 g, 0.16 mmol) and copper(I) iodide (30 mg, 0.16 mmol) was purged with N2. (2R)-but-3-yn-2-ol (0.13 g, 1.9 mmol) and triethylamine (4.5 mL, 33 mmol) was added via syringe. The reaction mixture was heated at reflux for 2 h. The mixture was concentrated under reduced pressure, and the resultant residue was purified on silica gel (eluting with 0-85% EtOAc/hexanes) to give the desired product. LCMS calculated for C11H9ClNOS (M+H)+: m/z=238.0. Found: 238.0.
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