Triethylsilane → HCID 21963517, compound
Reaction equation
C([SiH](CC)CC)C.[Br:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([F:22])[CH:13]=1)=O>FC(F)(F)C(O)=O>[Br:8][CH2:9][CH2:10][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([F:22])[CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Triethylsilane (1.60 mL, 10.017 mmol) was added via syringe to a stirred solution of N-[4-{2-bromo-acetyl)-2-fluoro-phenyl]-acetamide (1.1435 g, 4.172 mmol) in trifluoroacetic acid (14.0 mL) under nitrogen. The reaction was heated on an oil bath to 60° C. After 2.5 h, the reaction mixture was poured into ice water and allowed to warm to rt. The crude product was extracted with methylene chloride (2×75 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was crystallized from methanol and water to provide 0.6109 g (2.349 mmol) of the product as a white solid. Yield: 56%; MS (APCI): 260 [M+H]+, 262 [M+H+2]+; 1H NMR (400 MHz, CDCl3) δ 8.22 (dd, J=8.3, 8.5 Hz, 1H), 7.30 (br s, 1H), 6.93–6.97 (m, 2H), 3.51 (t, J=7.3 Hz, 2H), 3.10 (t, J=7.3 Hz, 2H), 2.20 (s, 3H).