Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1.C(N(CC)C(C)C)(C)C.N#N.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[C:64]1([SH:70])[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>CCOC(C)=O.[OH-].[Na+].O1CCOCC1>[C:64]1([S:70][C:2]2[CH:3]=[CH:4][C:5]3[O:9][CH:8]=[N:7][C:6]=3[CH:10]=2)[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1A 150 mL pressure bottle was charged with 5-bromobenzo[d]oxazole (2.43 g, 12.3 mmol), N,N-diisopropylethylamine (4.28 mL, 24.5 mmol), and 24 mL dioxane. N2 was bubbled through the solution for 3 min, at which point tris(dibenzylidineacetone)palladium(0) (0.281 g, 0.307 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.355 g, 0.614 mmol), and benzenethiol (1.26 mL, 12.3 mmol) were added. The dark brown solution was sealed and heated to 100° C. overnight. The mixture was diluted with EtOAc and NaOH, and the organic layer was extracted 2×1N NaOH. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give an orange oil, which was purified by ISCO, 0-100% 10% EtOAc/hexanes in hexanes to give 5-(phenylthio)benzo[d]oxazole as an orange oil. MS (ESI) m/z: Calculated: 227.0; Observed: 228.0 (M++1).
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