bromo(triethyl)silane

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

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: 284 mg (1 mmol) of 11β-methoxy-estra-1,3,5(10),16-tetraen-3-ol is reacted in 10 ml of tert-butylmethyl ether and 1 ml of pyridine with 0.6 ml of triethylbromosilane. After 1 hour, 30 ml of water is added to the reaction suspension. The organic phase is separated, washed, dried and concentrated by evaporation in a vacuum. The oily product that is thus obtained is used immediately in the next stage (hydroboration). Yield: 380 mg (95% of theory) The organic phase is separated washed dried concentrated by evaporation in a vacuum The oily product that is thus obtained

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

Procedure: 284 mg (1 mmol) of 11β-methoxy-estra-1,3,5(10),16-tetraen-3-ol is reacted in 10 ml of tert-butylmethyl ether and 1 ml of pyridine with 0.6 ml of triethylbromosilane. After 1 hour, 30 ml of water is added to the reaction suspension. The organic phase is separated, washed, dried and concentrated by evaporation in a vacuum. The oily product that is thus obtained is used immediately in the next stage (hydroboration). Yield: 380 mg (95% of theory) The organic phase is separated washed dried concentrated by evaporation in a vacuum The oily product that is thus obtained

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

Procedure: 284 mg (1 mmol) of 11β-methoxy-estra-1,3,5(10),16-tetraen-3-ol is reacted in 10 ml of tert-butylmethyl ether and 1 ml of pyridine with 0.6 ml of triethylbromosilane. After 1 hour, 30 ml of water is added to the reaction suspension. The organic phase is separated, washed, dried and concentrated by evaporation in a vacuum. The oily product that is thus obtained is used immediately in the next stage (hydroboration). Yield: 380 mg (95% of theory) The organic phase is separated washed dried concentrated by evaporation in a vacuum The oily product that is thus obtained

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

Procedure: 160 mg (0.37 mmol) of dimethyl N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-α-(ethylamino)ethylphosphonate are dissolved in 8 ml of dichloromethane and stirred at room temperature for one hour with 0.19 ml (4 eq.) of triethylbromosilane. The solvent and excess reagent are evaporated and the residue is briefly dried in a high vacuum, dissolved in 5 ml of an about 33% hydrogen bromide solution in acetic acid, and stirred at room temperature for 18 hours. The reaction mixture is diluted with diethyl ether, and the solid is filtered off, washed with diethyl ether and dried. The title compound is obtained as a beige solid; m.p.=191° (dec.). The solvent and excess reagent are evaporated the residue is briefly dried in a high vacuum dissolved in 5 ml of an about 33% hydrogen bromide solution in acetic acid The reaction mixture is diluted with diethyl ether the solid is filtered off washed with diethyl ether dried

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 3-(4-(oxiran-2-yl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole (205 mg, 0.549 mmol) in THF (5 mL) at −78° C. was slowly added bromotriethylsilane (100 μL, 0.582 mmol). The reaction mixture was stirred for 1 hour at −78° C. LC/MS was employed to determine extent of reaction. An aliquot was removed and concentrated in vacuo. Crude NMR indicated mostly desired regioisomer. The reaction was quenched with water and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated. The solids were purified on a silica cartridge using an EtOAc/hexanes gradient to yield 130 mg of Preparation 1C as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.16-8.24 (2H, m), 7.72-7.81 (2H, m), 7.61 (2H, m, J=8.13 Hz), 7.49-7.58 (3H, m), 5.12 (1H, dd, J=7.47, 5.93 Hz), 4.09-4.17 (1H, m), 4.01-4.08 (1H, m), 2.97-3.05 (2H, m), 1.70-1.83 (2H, m), 1.06 (3H, t=7.36 Hz). extent of reaction An aliquot was removed concentrated in vacuo The reaction was quenched with water extracted with EtOAc The organic layer was dried with MgSO4 filtered concentrated The solids were purified on a silica cartridge to yield

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

Procedure: β-D-Galactose pentaacetate (5.00 g, 12.8 mmol) and bismuth(III) bromide (287 mg, 640 μmol) were dissolved in dichloromethane (25 mL), the solution was added with bromotriethylsilane (6.76 mL, 51.2 mmol), and the mixture was stirred at room temperature for 3 hours under an argon atmosphere. The reaction mixture was poured into aqueous saturated sodium hydrogencarbonate cooled on ice, then the mixture was extracted with dichloromethane, and the organic layer was washed with brine. The organic layer was dried over sodium sulfate, and the solvent was removed to obtain 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (5.30 g, quantitative). cooled on ice the mixture was extracted with dichloromethane the organic layer was washed with brine The organic layer was dried over sodium sulfate the solvent was removed