Cesium carbonate → HCID 67248215, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask containing 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (402 mg, 1.7 mmol), ethyl 4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxy-2-methylcyclohexanecarboxylate (400 mg, L1 mmol), Pd2(dba)3 (105 mg, 0.11 mmol), X-phos (55 mg, 0.11 mmol) and Cs2CO3 (1.12 g, 3.45 mmol) was added 4.3 mL of degassed 10:1 1,4 dioxane/H2O. The reaction was heated to 100° C. for 16 h, then cooled and partitioned between EtOAc (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The layers were separated and the aqueous phase was extracted once with EtOAc (50 mL). The combined organic phases were washed with brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification of the resulting residue on silica furnished ethyl 4-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]-4-hydroxy-2-methylcyclohexanecarboxylate (344 mg, 80%) as a colorless foam. MS BSI: [M+H]+ m/z 375.2.

Provenance & Evidence