Trimethylsilyl iodide → HCID 21190089, compound

HRID 619435Notes

Reaction equation

HRID 619435 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([C:26](OC(C)(C)C)=[O:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])[N:6]2[C:33]=1C(=O)C(Cl)(Cl)Cl)[CH3:2].I[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[N:4]=[C:5]2[N:6]3[C:7]([CH2:11][N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]([F:25])([F:23])[F:24])(=[O:20])=[O:21])[C:26](=[O:27])[C:33]=13)=[CH:8][CH:9]=[CH:10]2)[CH3:2]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 21190286HCID 21190286, compound

Product 1

HCID 21190089HCID 21190089, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.73 g (2.71 mmol) of 2-ethyl-3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-[5-(trifluoromethanesulfonamido)pentan-1-yl]aminomethyl]imidazo[1,2-a]pyridine in 15 ml of chloroform was added dropwise 0.80 ml (5.42 mmol) of iodotrimethylsilane at room temperature. The reaction mixture was stirred for 10 minutes, which was poured into ice-water, followed by neutralization with a saturated aqueous solution of sodium hydrogencarbonate. This solution was extracted with 100 ml of ethyl acetate. The organic layer was washed with 50 ml of 1.0N aqueous solution of sodium thiosulfate, then with 50 ml of a saturated aqueous saline solution. The organic layer was dried over magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1) to give 603 mg of the desired compound (52.3%, pale yellow solid).

Workup

  1. extractionThis solution was extracted with 100 ml of ethyl acetate
  2. washThe organic layer was washed with 50 ml of 1.0N aqueous solution of sodium thiosulfate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-05bad01cb3a1489ba8e66623721f1f24
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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