Reaction #40552

Reaction equation

2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

sodium carbonate

6-Chloro-4-[6-chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

→

4-[6-Chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(4-hydroxy-3,5-dimethyl phenyl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Solvents

DME

Conditions

Workup

1. 1
   Otheris passed in for 10 min
2. 2
   OtherThe volatile constituents are removed in vacuo
3. 3
   Otherthe product is purified by column chromatography (RP-HPLC, gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

Procedure

6-Chloro-4-[6-chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (100 mg; 0.185 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.15 equivalents) are dissolved in DME, and argon is passed in for 10 min. 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1 equivalent) and 2M aqueous sodium carbonate solution (2 equivalents) are added and the mixture is heated at 95° C. for 5 hours. The volatile constituents are removed in vacuo, the residue is taken up in DMF, and the product is purified by column chromatography (RP-HPLC, gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)).

Source