indium

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:

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:

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

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

Procedure: To a mixed solution of sodium iodide (2080 mg, 13876 μmol), indium (2000 mg, 6938 μmol, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and 1-bromo-3-methylbut-2-ene (1616 μL, 13876 μmol, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in DMF (30 mL), was added 21.3 (1593 mg, 13876 μmol). The mixture was stirred at room temperature for 1 hour and then diluted with EtOAc and water. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to give a residue which was purified by CombiFlash® chromatography to give the product as an oil (2.30 g, 92%). MS ESI m/e: 376.1 (M+18)+. The organic phase was washed with water and brine dried over anhydrous sodium sulfate After filtration the organic solvent was removed in vacuo to give a residue which was purified by CombiFlash® chromatography

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

Procedure: To a mixed solution of sodium iodide (2080 mg, 13876 μmol), indium (2000 mg, 6938 μmol) and 1-bromo-3-methylbut-2-ene (1616 μL, 13876 μmol) in DMF (30 mL), was added T30.3 (1593 mg, 13876 μmol). The mixture was stirred at room temperature for 1 hour, and then was diluted with EtOAc and water. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to give a residue which was purified by chromatography to give the product as an oil (2.30 g, 92%). MS ESI m/e: 376.1 (M+18)+. The organic phase was washed with water and brine dried over anhydrous sodium sulfate After filtration the organic solvent was removed in vacuo to give a residue which was purified by chromatography

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

Procedure: The compound of Example 16G (2.5 g, 5.2 mmol) was dissolved in 20 mL of water and 30 mL of tetrahydrofuran. Indium powder (0.90 g) was added followed by formaldehyde (37% aqueous solution, 1.6 mL, 21 mmol). Two additional portions of indium (0.3 g each) were added to drive the reaction toward completion. The reaction was diluted with 180 mL of water and extracted twice with 250 mL each of ethyl acetate. The combined organic layers were washed sequentially with 5% NaHCO3 and brine, then dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (200 mL of SiO2, elution with a gradient of 1:1 to 3:1 ethyl acetate:hexanes) afforded the titled compound (0.97 g, 68%). the reaction toward completion extracted twice with 250 mL each of ethyl acetate The combined organic layers were washed sequentially with 5% NaHCO3 and brine dried over MgSO4 filtered concentrated in vacuo Purification by silica gel chromatography ( 200 mL of SiO2, elution with a gradient of 1:1 to 3:1 ethyl acetate