Trimethylsilyl iodide → HCID 76684536, compound

HRID 925216Notes

Reaction equation

HRID 925216 reaction equation
C(OC([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[CH:12]([CH2:20][CH3:21])[C:13]([F:19])([F:18])[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>[CH2:20]([CH:12]1[C:11]2[C:10]3[CH2:22][CH2:23][NH:6][CH2:7][CH2:8][C:9]=3[CH:17]=[CH:16][C:15]=2[CH2:14][C:13]1([F:19])[F:18])[CH3:21]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86725328HCID 86725328, compound

Product 1

HCID 76684536HCID 76684536, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Into a glass vial containing the product from step (b) (42 mg, 0.130 mmol) dissolved in CHCl3 (2 ml), TMSI (176 μL, 1.3 mmol) was added. The stirred reaction mixture was heated to 60° C. for 2 hours. The volatiles were evaporated in vacuo and 2M HCl (2 ml) and water (20 ml) were added. The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo give the title compound as a colorless semi-solid (16 mg). 1H NMR (300 MHz, CDCl3) 7.00-6.93 (m, 2H); 3.43-3.21 (m, 3H); 2.96-2.86 (m, 8H); 2.20 (bs, 1H); 1.75-1.62 (m, 2H); 0.92 (t, J=7.5 Hz, 3H); MS: ESI (positive): 252 (M+1).

Workup

  1. customThe stirred reaction mixture
  2. customThe volatiles were evaporated in vacuo and 2M HCl (2 ml) and water (20 ml)
  3. additionwere added
  4. washThe aqueous mixture was washed with diethyl ether (2×)
  5. extractionextracted with DCM (3×)
  6. washThe combined DCM extracts were washed with brine
  7. dry with materialdried over Na2SO4, and solvent
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-6fd9f749e59b483e82222959197413f3
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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