Trimethylsilyl iodide → HCID 9801813, compound

HRID 619429Notes

Reaction equation

HRID 619429 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:28]([O:30]C(C)(C)C)=O)[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[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:25][C:24]([F:26])([F:27])[S:21]([NH: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:28]1=[O:30])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 21190147HCID 21190147, compound

Product 1

HCID 9801813HCID 9801813, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5.25 g (8.81 mmol) of 3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-[4-(trifluoromethanesulfonamido)butan-1-yl]aminomethyl]imidazo[1,2-a]pyridine in 25 ml of chloroform was added dropwise 2.5 ml (17.62 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 250 ml of ethyl acetate. The organic layer was washed with 100 ml of 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, then the solvent was distilled off under reduced pressure. The residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1) to give 2.16 g (65.0%) of the desired compound.

Workup

  1. extractionThis solution was extracted with 250 ml of ethyl acetate
  2. washThe organic layer was washed with 100 ml of a 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-4d2a42ddb1834887b38317a18313ae47
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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