Imidazole → HCID 69671630, compound

To a solution of 2-bromo-5-iodobenzoic acid (11.4 g, 34.8 mmol) in dichloromethane (140 mL) was added methanol (17 mL) followed by trimethylsilyldiazomethane solution (2M in hexanes, 19.2 mL, 38.4 mmol). The reaction was stirred at room temperature for twelve hours, quenched by the dropwise addition of acetic acid (5 mL) and thoroughly concentrated. The resulting residue was dissolved in tetrahydrofuran. To this solution was added diisobutylaluminum hydride solution (1M in DCM, 50 mL, 50 mmol) and the reaction was stirred at room temperature. After sixteen hours, more diisobutylaluminum hydride solution (1M in DCM, 50 mL, 50 mmol) was added. After 96 more hours at room temperature the reaction was diluted with ether (100 mL) and quenched by the sequential addition of water (4 mL), 15% aqueous NaOH solution (4 mL) and water (10 mL). After thirty minutes the mixture was filtered through Celite and the filtrate was concentrated. The resulting residue was dissolved in dimethylformamide (75 mL). To this solution was added imidazole (6.1 g, 89.6 mmol) and t-butyldimethylchlorosilane (6.8 g, 45.1 mmol). The reaction was stirred at room temperature for two hours and then diluted with ethyl acetate. The organics were washed with saturated aqueous NH4Cl solution, water and brine. The organic layer was dried (MgSO4) and concentrated, and the resulting residue was purified by flash column chromatography to yield (2-bromo-5-iodobenzyloxy)-(tert-butyl)dimethylsilane (9.2 g, 62%).

1. customquenched by the dropwise addition of acetic acid (5 mL)
2. concentrationthoroughly concentrated
3. dissolutionThe resulting residue was dissolved in tetrahydrofuran
4. stirringthe reaction was stirred at room temperature
5. waitAfter sixteen hours
6. customquenched by the sequential addition of water (4 mL), 15% aqueous NaOH solution (4 mL) and water (10 mL)
7. filtrationAfter thirty minutes the mixture was filtered through Celite
8. concentrationthe filtrate was concentrated
9. dissolutionThe resulting residue was dissolved in dimethylformamide (75 mL)
10. stirringThe reaction was stirred at room temperature for two hours
11. washThe organics were washed with saturated aqueous NH4Cl solution, water and brine
12. dry with materialThe organic layer was dried (MgSO4)
13. concentrationconcentrated
14. customthe resulting residue was purified by flash column chromatography

ORD record

ord-0dba706cef954a1ba79af5efaf94b084

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156823B2