Triethylsilane → HCID 21963517, compound

HRID 2211903Notes

Reaction equation

HRID 2211903 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]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 13355716HCID 13355716, compound

Product 1

HCID 21963517HCID 21963517, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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).

Workup

  1. temperatureto warm to rt
  2. extractionThe crude product was extracted with methylene chloride (2×75 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was crystallized from methanol and water

Sources & evidence

ORD record
ord-3e609e55186c4c97810bca83251b5a47
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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