Acetonitrile → HCID 68667474, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(dihydroxyboryl)thiophene-2-carboxylic acid (1.89 g, 10.85 mmol) and 1-bromo-4-iodo-2-methoxybenzene (3.09 g, 9.86 mmol) in a 3:1 mixture of MeCN:H2O (100 mL) was treated with K2CO3 (4.09 g, 29.6). Pd(OAc)2 (66.4 mg, 0.30 mmol) and biphenyl-2-yl(dicyclohexyl)phosphine (207 mg, 0.59 mmol) were added and the mixture was stirred at 90° C. for 3 h. The mixture was cooled and concentrated, and the residue was added at 0° C. to a mixture of 10% aqueous NaOH (100 mL) and DCM. The mixture was acidified to pH=1 by addition of aqueous HCl (6 N) and the solid precipitate was collected by filtration, washed with cold H2O and DCM, then dried to afford the title compound (2.29 g, 74%). LCMS (ES+) m/z 313, 315 (M+H)+.

Provenance & Evidence