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-85b768e56f0b4e74b5b74d6a5ff43a13

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06921756B2