Trimethylsilyl iodide → HCID 21190167, compound

HRID 619432Notes

Reaction equation

HRID 619432 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:29]([O:31]C(C)(C)C)=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.I[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:27][C:25]([F:26])([F:28])[S:22]([NH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[CH2:14][C:10]2[N:9]3[C:5](=[CH:6][N:7]=[C:8]3[CH:13]=[CH:12][CH:11]=2)[C:29]1=[O:31])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 21190277HCID 21190277, compound

Product 1

HCID 21190167HCID 21190167, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.75 g (2.87 mmol) of 3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-[5-(trifluoromethanesulfonamido)pentan-1-yl]aminomethyl]imidazo[1,2-a]pyridine in 25 ml of chloroform was added dropwise 0.82 ml (5.74 mmol) of iodotrimethylsilane at room temperature. The reaction mixture was stirred for 15 minutes, which was poured into ice-water, followed by neutralization with a saturated aqueous solution of sodium hydrogencarbonate. This solution was extracted with 150 ml of ethyl acetate. The organic layer was washed with a 1.0N aqueous solution of sodium thiosulfate, then with 100 ml of a saturated aqueous saline solution. The organic layer was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1) to give 706 mg of the object product (63.1%, pale yellow solid substance).

Workup

  1. extractionThis solution was extracted with 150 ml of ethyl acetate
  2. washThe organic layer was washed with a 1.0N aqueous solution of sodium thiosulfate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-b9a1c33b0d214b869acf52f875de95e1
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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