Tri-o-tolylphosphine → HCID 59812013, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7 (129.7 mg, 0.186 mmol), 3-bromo-4-methylthiophene (30 μL, 0.30 mmol), PdCl2(MeCN)2 (4.8 mg, 18.6 μmol), tri-o-tolylphosphine (11.4 mg, 37.5 μmol) in toluene (1.7 mL) was stirred under N2 at 85° C. overnight. The reaction mixture was cooled to r.t., diluted with AcOEt (3 mL), and extracted with 10% aqueous HCl ((4×0.5 mL). combined aqueous solutions were washed with CH2Cl2 (2 mL), and basified with 10% aqueous NaOH (2.5 mL). The mixture was extracted with CH2Cl2:MeOH=19:1 (4×3 mL). Combined extracts were washed with brine, dried (MgSO4), and concentrated in vacuum. The residue was purified by preparative TLC using CH2Cl2:MeOH=19:1 as eluent to afford 8 (12.9 mg, 21%) as tan solid. 1H NMR (400 MHz, CDCl3) δ 2.34 (d, J=1.0 Hz, 3H), 3.01 (s, 6H), 6.85 (d, J=8.9 Hz, 2H), 7.10 (dq, J=3.3, 1.0 Hz, 1H), 7.36 (d, J=3.3 Hz, 1H), 7.41 (d, J=1.2 Hz, 1H), 7.53 (d, J=8.9 Hz, 2H), 8.14 (d, J=2.1 Hz, 1H), 8.59 (d, J=2.1 Hz, 1H), 10.00 (bs, 1H).

Provenance & Evidence