(2-bromophenyl)methoxy-tert-butyl-dimethylsilane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 450 mg of (2-bromobenzyloxy)-tert-butyldimethylsilane, 500 mg of 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine and 1.46 g of caesium carbonate are dissolved in 8 ml of tetrahydrofuran and 1 ml of water. The mixture is degassed with argon for 10 min, 110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added and the mixture is heated at the reflux of the solvent for 16 hours. After cooling, the reaction mixture is hydrolysed with water, and the organic phase, which has been extracted with dichloromethane, is separated, dried and concentrated under reduced pressure. The oil obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 260 mg of compound are obtained. The mixture is degassed with argon for 10 min 110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added the mixture is heated at the reflux of the solvent for 16 hours After cooling the organic phase, which has been extracted with dichloromethane is separated dried concentrated under reduced pressure The oil obtained is purified by silica gel chromatography, elution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.0 g of (2-bromophenyl)methanol are placed in a round-bottomed flask and dissolved in 100 ml of tetrahydrofuran. 1.1 g of 1H-imidazole are added thereto, followed by 2.1 g of tert-butyldimethylsilane chloride, and the mixture is left to stir at ambient temperature for 48 hours. The reaction mixture is then hydrolysed with water, and the organic phase, which has been extracted with ethyl acetate, is separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 2.66 g of compound are obtained. the mixture is left hydrolysed with water, and the organic phase, which has been extracted with ethyl acetate is separated dried over magnesium sulphate concentrated under reduced pressure The residue obtained is purified by silica gel chromatography, elution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromobenzyl alcohol (25.0 g) was dissolved in N,N-dimethylformamide (150 ml) and imidazole (20.0 g) and tert-butyldimethylchlorosilane (22.2 g) were added. The reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 5% aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed successively with 5% aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (40.9 g). extracted with ethyl acetate The organic layer was washed successively with 5% aqueous sodium hydrogencarbonate solution, water and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure