Bromotrimethylsilane → HCID 22179271, compound

To a solution of [(2-thiophenesulfonyl-N-methylamino)methyl]-phosphonic acid dimethyl ester (obtained as described in Example 46, step 2) (180 mg, 0.6 mmol) in dichloromethane (3 mL) at 0° C. was slowly added bromotrimethylsilane (190 μL, 1.4 mmol). The reaction was gradually warmed to room temperature and allowed to stir overnight. The reaction mixture was concentrated, the residue was redissolved in dichloromethane, and the solution was again concentrated. Methanol (10 mL) was added to the residue, and the solution was stirred at room temperature for 30 min. The solution was then filtered and concentrated. The oily residue was triturated with 1:1 ether-hexanes, and an orange solid was collected by filtration. The orange solid was boiled in dichloromethane (3 mL), cooled, and filtered to yield the title compound (120 mg, 74%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 7.87 (dd, J=1.5, 4 Hz, 1H, Ar—H), 7.66 (dd, J=1.5, 3.5 Hz, 1H, Ar—H), 7.25 (dd, J=4, 5 Hz, 1H, Ar—H), 3.31 (d, J=12.5 Hz, 2H, CH2P), 2.92 (s, 3H, NCH3).

1. customat 0° C.
2. concentrationThe reaction mixture was concentrated
3. dissolutionthe residue was redissolved in dichloromethane
4. concentrationthe solution was again concentrated
5. additionMethanol (10 mL) was added to the residue
6. stirringthe solution was stirred at room temperature for 30 min
7. filtrationThe solution was then filtered
8. concentrationconcentrated
9. customThe oily residue was triturated with 1:1 ether-hexanes
10. filtrationan orange solid was collected by filtration
11. temperaturecooled
12. filtrationfiltered

ORD record

ord-110dbbbedf17439cabe97774769d459e

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514556B2