Sodium Iodide → HCID 69195672, compound

Temperature

150 °C

A stirred suspension of (3-chlorophenyl)(8-chloro-3-quinolinyl)methanol (D2)(1.4 g, 4.6 mmol), trimethylsilyl chloride (3.5 ml, 28 mmol) and sodium iodide (4.2 g, 28 mmol) in acetonitrile (28 ml) was heated in a sealed tube in a microwave oven at 150° C. for 35 mins. The mixture was filtered and the solid washed with dichloromethane (5 ml) and diethyl ether (5 ml). The filtrate and washings were concentrated in vacuo to a dark brown solid, which was redissolved in dichloromethane (75 ml) and the solution washed with 10% aqueous sodium sulfite solution (75 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of acetone/toluene to give the title compound (D3) as a pale yellow solid (1.04 g, 3.6 mmol, 78%).

1. filtrationThe mixture was filtered
2. washthe solid washed with dichloromethane (5 ml) and diethyl ether (5 ml)
3. concentrationThe filtrate and washings were concentrated in vacuo to a dark brown solid, which
4. dissolutionwas redissolved in dichloromethane (75 ml)
5. washthe solution washed with 10% aqueous sodium sulfite solution (75 ml)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo to an oil
8. customThe oil was purified by chromatography over silica gel eluting with a gradient of acetone/toluene

ORD record

ord-fab253737dc24831860e4406f5d62354

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439243B2