Dimethylformamide → HCID 57989086, compound

tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane [Aromatic Intermediate 24, step b] (4.4 g) was added dropwise over 5 min to a solution of sec-butyllithium (1.4M in cyclohexane, 11.7 mL) and 1,1,4,7,7-pentamethyldiethylenetriamine (3.4 mL) in THF (25 mL) at −78° C. The resulting mixture was stirred for 2 h, then DMF (6.4 mL) was cautiously added and the resulting mixture allowed to warm to RT and stirred overnight. The reaction was quenched with water (100 mL) and then ethyl acetate (250 mL) was added. The phases were separated and the organic phase washed with water (2×100 mL), aqueous HCl (2M, 2×50 mL), and brine (100 mL), then dried over magnesium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with isohexane to 10% ether in isohexane gradient. The fractions containing product were combined and evaporated to give the titled compound as a clear oil. Yield 1.0 g.

1. stirringstirred overnight
2. customThe reaction was quenched with water (100 mL)
3. additionethyl acetate (250 mL) was added
4. customThe phases were separated
5. washthe organic phase washed with water (2×100 mL), aqueous HCl (2M, 2×50 mL), and brine (100 mL)
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. customevaporated
9. customPurification
10. washeluting with isohexane to 10% ether in isohexane gradient
11. additionThe fractions containing product
12. customevaporated

ORD record

ord-75385ea1df3d4647a01c299b1317e5eb

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455483B2