Sodium Carbonate → 3′-Chloro-2-(trifluoromethyl)[1,1′-biphenyl]-4-amine

Participants

Reaction Steps

A mixture of 5-amino-2-bromobenzotrifluoride (Dakwood Products, Inc.) (500 mg, 2.1 mMol), 3-chlorophenylboronic acid (970 mg, 6.2 mMol, 3 equiv) (Aldrich), Pd(PPh3)4 (70 mg, 0.018 mMol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 5 mL, 10 mMol, 4.76 equiv), and toluene (14 mL) is stirred at reflux for 1 h. The reaction mixture is allowed to cool to rt and filtered through a pad of celite, washing the filter cake with CH2Cl2 and H2O. The layers are separated and the aqueous phase is extracted with CH2Cl2 (2×60 mL). The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. MPLC (CH3CN/H2O/TFA) purification of the crude material affords the title compound: MS: 270.0 [M-2]−; HPLC DtRet=4.9.

Provenance & Evidence