Trimethylsilyl iodide → HCID 21190065, compound

HRID 1068769Notes

Reaction equation

HRID 1068769 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:32](OC(C)(C)C)=[O:33])[C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[CH:18][CH:17]=3)=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.C[Si](I)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:29][C:28]([F:31])([F:30])[S:25]([NH:24][CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([N:15]2[CH2:14][C:10]3[N:9]4[C:5](=[CH:6][N:7]=[C:8]4[CH:13]=[CH:12][CH:11]=3)[C:32]2=[O:33])=[CH:21][CH:20]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 21190083HCID 21190083, compound

Product 1

HCID 21190065HCID 21190065, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 644 mg (1.00 mmol) of 3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-[4-(2-trifluoromethanesulfonamidoethan-1-yl)phenyl]aminomethyl]imidazo[1,2-a]pyridine in 5 ml of chloroform was added dropwise 0.29 ml (2.00 mmol) of trimethylsilyl iodide at room temperature. The reaction mixture was stirred for 30 minutes at room temperature, and poured into ice-water. The mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. To the mixture was added 50 ml of chloroform for extraction of the desired compound. The organic layer was washed with 50 ml of a saturated aqueous saline solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1) to afford 195.7 mg of the desired compound (46.1%, a pale yellow solid).

Workup

  1. extractionfor extraction of the desired compound
  2. washThe organic layer was washed with 50 ml of a saturated aqueous saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-f3db95d7317649d2be274417c5926e31
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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