Trimethylsilyl iodide → HCID 76684635, compound

HRID 925192Notes

Reaction equation

HRID 925192 reaction equation
C(OC([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[CH:12]([CH3:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[CH3:18][CH:12]1[C:11]2[C:10]3[CH2:19][CH2:20][NH:6][CH2:7][CH2:8][C:9]=3[CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86725307HCID 86725307, compound

Product 1

HCID 76684635HCID 76684635, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Into a glass vial, the product from step (c) dissolved in CHCl3 (3 ml) was placed. To this solution, TMSI (0.31 ml, 2.3 mmol) was added. The reaction mixture was heated to 60° C. for 4 h and then allowed to cool to room temperature. The reaction mixture was quenched by addition of 2N HCl (5 ml) and further diluted with water (25 ml). The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was basified by addition of 5N KOH to pH 10. The basic solution was extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title product. 1H NMR (CDCl3) δ 6.95 (d, J=7.5 Hz, 1H), 6.90 (d, J=7.5 Hz, 1H), 3.36-3.27 (m, 1H), 3.08-2.90 (m, 7H), 2.82-2.74 (m, 1H), 2.27-2.16 (m, 1H), 1.89 (bs, 1H), 1.80-1.73 (m, 1H), 1.33-1.22 (m, 2H), 1.12 (d, J=6.9 Hz, 3H); MS: ESI (positive): 202 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. customThe reaction mixture was quenched by addition of 2N HCl (5 ml)
  3. additionfurther diluted with water (25 ml)
  4. washThe aqueous mixture was washed with diethyl ether (2×)
  5. additionThe aqueous layer was basified by addition of 5N KOH to pH 10
  6. extractionThe basic solution was extracted with DCM (3×)
  7. washThe combined DCM extracts were washed with brine
  8. dry with materialdried over Na2SO4, and solvent
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-58b3d83de151473e9306574500355429
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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