Methyl iodide → HCID 57582345, compound

To a stirred solution of 4-chloro-3-bromophenyl-methanol (cited in Amgen patent WO03099776) (900 mg, 4.06 mmol) in 2-methyl-tetrahydrofuran (15 ml) was added potassium hydroxide (912 mg, 16.3 mmol) and the resulting suspension was stirred at room temperature for 30 minutes. Iodomethane (1.01 ml, 4.00 mmol) was then added and the reaction was stirred for 16 hours at room temperature. LCMS indicated incomplete reaction. Potassium hydroxide (912 mg, 16.3 mmol) was added and the resulting mixture stirred for 5 minutes before adding further iodomethane (4.04 ml, 16 mmol) and stirring was continued for 3 hours at room temperature. Ethyl acetate (60 ml) and saturated brine solution (30 ml) were added and the layers were separated. The organic extract was further washed with saturated brine solution (2×30 ml) then dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo to afford the crude title compound as a yellow oil (901 mg, 94%).

1. stirringthe reaction was stirred for 16 hours at room temperature
2. customreaction
3. stirringthe resulting mixture stirred for 5 minutes
4. stirringstirring
5. waitwas continued for 3 hours at room temperature
6. customthe layers were separated
7. extractionThe organic extract
8. washwas further washed with saturated brine solution (2×30 ml)
9. dry with materialthen dried over anhydrous MgSO4 (s)
10. filtrationfiltered
11. customevaporated in vacuo

ORD record

ord-267179f55ba24baf8b8fa5d39c8a28d4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2