Trimethylsilyl iodide → HCID 76684539, compound

HRID 925219Notes

Reaction equation

HRID 925219 reaction equation
C(OC([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12]([CH3:21])([CH3:20])[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>[F:19][C:13]1([F:18])[C:12]([CH3:20])([CH3:21])[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]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86725332HCID 86725332, compound

Product 1

HCID 76684539HCID 76684539, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Into a glass vial containing the product from step (c) (20 mg, 0.061 mmol) dissolved in CHCl3 (2 ml), TMSI (84 μL, 0.619 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours. The volatiles were evaporated in vacuo and the residue diluted with 2M HCl (2 ml) and water (20 ml). 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 to give the title compound as a colorless oil (4.7 mg). 1H NMR (300 MHz, CDCl3) δ 6.99-6.96 (m, 2H); 3.28 (t, J=14.1 Hz, 2H); 3.03-2.90 (m, 8H); 1.89 (bs, 1H); 1.39 (s, 6H); MS: ESI (positive): 252 (M+1).

Workup

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

Sources & evidence

ORD record
ord-eeb9c80507bb4451995fb002fb13d26d
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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