HCID 178418332, compound → HCID 178448945, compound

Temperature

7.5 °C

This compound was prepared using methodology described in Synthesis 1999, 2138-2144. To a solution of 7.00 g (32.8 mmol) butyl-[1-(2-chloro-6-fluoro-phenyl)-meth-(E)-ylidene]-amine in 70 ml tetrahydrofuran at 0° C. was added 0.41 g (3.28 mmol) manganese(II) chloride. 21.8 ml (65.5 mmol) of a 3 M solution of methylmagnesium chloride in tetrahydrofuran was then added dropwise while the temperature of the reaction mixture was maintained at 5-10° C. After the addition was complete, the reaction mixture was stirred for a further 30 minutes, during which time the temperature rose to 40° C. (exotherm). The reaction mixture was then quenched by dropwise addition of water and stirred for a further 30 minutes before being diluted with toluene. The mixture was then filtered and the organic phase of the filtrate was then washed with saturated brine. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was resuspended in carbon tetrachloride and concentrated in vacuo again to afford 6.90 g (100%) of the title compound as a yellow oil which was used in the next step without further purification. MS (ISP): 212.1 ([{37Cl}M+H]+), 210.1 ([{35Cl}M+H]+).

1. customThis compound was prepared
2. customdescribed in Synthesis 1999, 2138-2144
3. additionAfter the addition
4. customrose to 40° C.
5. customThe reaction mixture was then quenched by dropwise addition of water
6. stirringstirred for a further 30 minutes
7. additionbefore being diluted with toluene
8. filtrationThe mixture was then filtered
9. washthe organic phase of the filtrate was then washed with saturated brine
10. customThe phases were separated
11. dry with materialthe organic phase was dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. concentrationconcentrated in vacuo again

ORD record

ord-d359ab68cb23475eb23e2d76f3ffc86b

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158668B2